Ammonium Hydroxide → N-[4-(3-Fluoro-benzyloxy)-phenyl]-malonamide

HRID 1884089Notes

Reaction equation

HRID 1884089 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[CH:10][CH:9]=1)=[O:6].[OH-].[NH4+:25]>O1CCCC1>[F:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:5](=[O:6])[CH2:4][C:3]([NH2:25])=[O:2])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10335956N-[4-(3-fluoro-benzyloxy)-phenyl]-malonamic acid methyl ester

Product 1

HCID 10017779N-[4-(3-Fluoro-benzyloxy)-phenyl]-malonamideYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

99 mg (0.31 mmol) N-[4-(3-fluoro-benzyloxy)-phenyl]-malonamic acid methyl ester (example 1) is dissolved in a mixture of 0.5 ml tetrahydrofuran and 1.0 ml of aqueous ammonium hydroxide (25%). The reaction vessel is capped and kept at 60° C. for 2.5 h. The reaction mixture is cooled, evaporated to dryness and diluted with water. Filtration provides 48 mg (51%) of the title compound as a light yellow solid. MS: m/e=303.2 (M++H).

Workup

  1. customThe reaction vessel is capped
  2. temperatureThe reaction mixture is cooled
  3. customevaporated to dryness
  4. additiondiluted with water
  5. filtrationFiltration

Sources & evidence

ORD record
ord-08ab74e0c2b549aa9401b0c0f718b0a4
Source dataset
uspto-grants-2004_07
Patent number
US06762320B2

Reaction notes

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