Ammonia → HCID 178429547, compound

HRID 2082947Notes

Reaction equation

HRID 2082947 reaction equation
[NH3:1].ClCC([O:6][CH2:7][CH3:8])=O.[C-:9]#[N:10].[Na+].[C:12]([O:18]CC)(=O)[CH2:13][C:14]([CH3:16])=O>O.CN(C)C=O>[OH:18][C:12]1[NH:1][C:7](=[O:6])[C:8]([C:9]#[N:10])=[C:14]([CH3:16])[CH:13]=1

Participants

7

Reactant 4

HCID 222Ammonia2×HCID 7751Ethyl chloroacetateHCID 8868Ethyl AcetoacetateHCID 8929Sodium Cyanide

Product 1

HCID 178429547HCID 178429547, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

92 Parts of an 18.5 percent strength by weight aqueous solution of ammonia are added to 122.5 parts of ethyl chloroacetate at from 10° to 15° C. After stirring for 2 hours, 200 parts of dimethylformamide and 167 parts of a 29.4 percent strength by weight solution of sodium cyanide in water are added. The reaction mixture is kept for 3 hours at 40° C, and 130 parts of ethyl acetoacetate are then added, followed by 139 parts of an 18.5 percent strength by weight aqueous ammonia solution. The mixtue is kept for 4 hours at 90° to 95° C. It is then worked up as described in Example 1. 10.2 parts of 2-hydroxy-5-cyano-4-methylpyrid-6-one (68% of theory, based on ethyl chloroacetate employed) of melting point 298°-302° C (with decomposition) are obtained.

Workup

  1. waitThe reaction mixture is kept for 3 hours at 40° C
  2. waitThe mixtue is kept for 4 hours at 90° to 95° C

Sources & evidence

ORD record
ord-df49de78f5b54b4087984f75a1eb2aa4
Source dataset
uspto-grants-1978_04
Patent number
US04083849

Reaction notes

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