6-Nitrophthalide → 6-Aminophthalide

HRID 647417

Reaction equation

HRID 647417 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][O:9][C:10]2=[O:11])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][O:9][C:10]2=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 2235846-Nitrophthalide

Product 1

HCID 936316-Aminophthalide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

6-Nitrophthalide (14.0 g; J A Houbion, J A Miles and J A Paton, Organic Preparations and Procedures International, 11 (1), 27, 1979) in solution in acetic acid was hydrogenated over a palladium on carbon catalyst to give 6-aminophthalide (12.0 g; W R Vaughan and S L Baird, J. Amer. Chem. Soc. 68, 1314, 1946). 6-Aminophthalide (10.0 g) was converted, via the diazonium salt intermediate, to 6-chlorophthalide (8.5 g; J Tirouflet, Bull. soc. sci. Bretagne Spec. No 26, 7, 1951).

Sources & evidence

ORD record
ord-5a62a9408ff34ee6a78fa088a07419eb
Source dataset
uspto-grants-1983_10
Patent number
US04409017

Linked notes

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