Hydrochloric Acid → N-[4-(3-fluoro-benzyloxy)-phenyl]-malonamic acid methyl ester

HRID 1884087Notes

Reaction equation

HRID 1884087 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5](Cl)=[O:6].[F:9][C:10]1[CH:11]=[C:12]([CH:22]=[CH:23][CH:24]=1)[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=1.Cl>ClCCl.N1C=CC=CC=1.O>[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5]([NH:21][C:18]1[CH:17]=[CH:16][C:15]([O:14][CH2:13][C:12]2[CH:22]=[CH:23][CH:24]=[C:10]([F:9])[CH:11]=2)=[CH:20][CH:19]=1)=[O:6]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 123460Methyl malonyl chlorideHCID 167753144-(3-Fluoro-benzyloxy)-phenylamine

Product 1

HCID 10335956N-[4-(3-fluoro-benzyloxy)-phenyl]-malonamic acid methyl esterYield 19.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 242 mg (1.77 mmol) chlorocarbonyl-acetic acid methyl ester in 2 ml dichloromethane is added dropwise to an ice-cooled solution of 350 mg (1.61 mmol) 4-(3-fluoro-benzyloxy)-phenylamine in 7 ml of pyridine. The mixture is then stirred for 2 h at room temperature, diluted with water, acidified with dil. hydrochloric acid and extracted with ethyl acetate. The organic phase is dried. Chromatography (silica gel, ethyl acetate/hexane 1:1) yields 99 mg (19%) of the title compound. Yellowish solid; MS: m/e=418.1 (M++H).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase is dried

Sources & evidence

ORD record
ord-1a593ffc941e4ecf9acb0e62221c1646
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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