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● Anilinas: clorambucilo (antineoplásico)<br />

CH 3OH, HCl<br />

esterificación<br />

(CH 2) 3CO 2CH 3<br />

O 2N<br />

HNO 3, H 2SO 4<br />

nitración<br />

e hidrólisis<br />

(CH 2) 3CO 2CH 3<br />

H 2O/<br />

O 2N<br />

1 H 2/Pd<br />

O<br />

2 HOCH2CH2 N<br />

(CH2) 3CO2CH3 HOCH2CH2 ClCH 2CH 2<br />

ClCH 2CH 2<br />

N<br />

(CH 2) 3CO 2CH 3<br />

H<br />

Hidrólisis<br />

H 2N<br />

ClCH 2CH 2<br />

ClCH 2CH 2<br />

(CH 2) 3CO 2H<br />

SOCl 2<br />

N<br />

Ar N<br />

Clorambucilo<br />

(CH 2) 3CO 2CH 3<br />

(CH 2) 3CO 2H<br />

99

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