2-Amino-4-nitrobenzaldehyde → 2,4-Diaminobenzaldehyde

HRID 5360Notes

Reaction equation

HRID 5360 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]>[Pd]>[NH2:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

3

Reactant 1

HCID 138911802-Amino-4-nitrobenzaldehyde

Product 1

HCID 111477482,4-Diaminobenzaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a manner similar to that described for 10-nitro-20(RS)- and 10-nitro-20(S)-camptothecin, a mixture of 2-amino-4-nitrobenzaldehyde is treated with the tricyclic ketone 11 yielding 11-nitro-20(RS)- or 11-nitro-20(S)-camptothecin which in turn is reduced to 11-amino compound camptothecin by palladium/carbon. Alternatively, the 11-amino-20(RS)- or 11-amino-20(S)-camptothecin is obtained by reaction of 2,4-diaminobenzaldehyde with ketone 11.

Sources & evidence

ORD record
ord-65534682ee6b4b1b840f36d71ebb8513
Source dataset
uspto-grants-1993_09
Patent number
US05244903

Reaction notes

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