5-Aminophthalide → 4-Aminophthalimide

HRID 1072763Notes

Reaction equation

HRID 1072763 reaction equation
C(C1C=C2C(=CC=1)C(=O)OC2)#[N:2].[NH2:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:19](=[O:20])[O:18][CH2:17]2.C([Cu])#N>>[NH2:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:19](=[O:20])[O:18][CH2:17]2.[NH2:13][C:14]1[CH:15]=[C:16]2[C:17](=[O:18])[NH:2][C:19](=[O:20])[C:21]2=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 7206695-AminophthalideHCID 8212181,3-Dihydro-1-oxoisobenzofuran-5-carbonitrile2×HCID 178418546HCID 178418546, compound

Product 2

HCID 729154-AminophthalimideHCID 7206695-Aminophthalide

Procedure

A method for the preparation of 5-cyanophthalide has previously been described in Bull. Soc. Sci. Bretagne, 1951, 26, 35 and in Levy and Stephen, J. Chem. Soc., 1931, 867. By this method 5-aminophthalide is converted to the corresponding 5-cyanophthalide by diazotation followed by reaction with CuCN. 5-Aminophthalide was obtained from 4-aminophthalimide by a two step reduction procedure.

Sources & evidence

ORD record
ord-dd20adba05ca44fbab12231b84b1252d
Source dataset
uspto-grants-2005_06
Patent number
US06911548B2

Reaction notes

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