Ammonia → HCID 14773390, compound

HRID 1722052Notes

Reaction equation

HRID 1722052 reaction equation
[CH2:1]([CH:8]1[CH2:17][C:16](=[O:18])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:19](OC)=O)[CH:14]=2)[O:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:23]>CO>[C:19]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[O:9][CH:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:17][C:16]2=[O:18])#[N:23]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 13850024HCID 13850024, compound

Product 1

HCID 14773390HCID 14773390, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-benzylchroman-4-one-6-carboxylate, the product of Preparation A33, is converted to the corresponding amide by the action of a molar excess of ammonia in aqueous methanol, recovered by simple stripping of the solvent and excess ammonia. In turn, the amide is converted to the title nitrile by the action of p-toluenesulfonyl chloride on a pyridine solution of the amide, according to the conditions of Stephens et al., J. Am. Chem. Soc., Vol. 77, pp 1701-1702 (1955). This product is well suited for the preparation of 6-cyano-c-4-hydroxy-r-2-benzylchroman-4-acetic acid by the methods of Examples above.

Workup

  1. customrecovered by simple stripping of the solvent and excess ammonia

Sources & evidence

ORD record
ord-b1f574ad9a8a4d37bc15c555f1b11f4e
Source dataset
uspto-grants-1989_08
Patent number
US04853410

Reaction notes

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