Pyridine → HCID 54717980, compound

HRID 464387Notes

Reaction equation

HRID 464387 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[C:12](=[O:23])[N:13]([CH3:22])[C:14]3[C:19]([C:20]=2[OH:21])=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:10])=[CH:4][CH:3]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OC(=O)C)(=O)C>O>[C:5]1([NH:8][C:9]([C:11]2[C:12](=[O:23])[N:13]([CH3:22])[C:14]3[C:19]([C:20]=2[OH:21])=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:10])[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1.[N:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54710916HCID 54710916, compound

Product 1

HCID 54717980HCID 54717980, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2 parts of N-(4-aminophenyl)-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide, 5 parts of pyridine, and 10 parts of acetic anhydride is left overnight at room temperature. Water is added and the precipitate is filtered off and washed with 2M aqueous hydrochloric acid, water, methanol and ethylether to give N-(4-acetylaminophenyl)-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide (1). M. p. 231°-4° C. (The same compound as 1:41.)

Workup

  1. filtrationthe precipitate is filtered off
  2. washwashed with 2M aqueous hydrochloric acid, water, methanol and ethylether

Sources & evidence

ORD record
ord-d9f1d685c68c49019154bec93cb2d70c
Source dataset
uspto-grants-1985_10
Patent number
US04547511

Reaction notes

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