Lithium Hydroxide → HCID 4737524, compound

HRID 2099997Notes

Reaction equation

HRID 2099997 reaction equation
C[O:2][C:3](=[O:21])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[Li+].[OH-]>O.CO>[C:13]([NH:12][C:9]1[CH:10]=[CH:11][C:6]([CH:5]=[CH:4][C:3]([OH:21])=[O:2])=[CH:7][CH:8]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 66958421HCID 66958421, compound

Product 1

HCID 4737524HCID 4737524, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(Method H5) A mixture of 3-(4-benzoylamino-phenyl)-acrylic acid methyl ester (4b) (1.650 g, 5.87 mmol) and LiOH (0.630 g, 15 mmol) in water (30 ml) and methanol (30 ml) was stirred at ambient temperature for 24 hours. Methanol was evaporated and the residue was treated with hydrochloric acid to pH 4. The resulting precipitate was filtered off, washed with water (3×20 ml), and dried to give the title compound as a white solid (1.443 g, 92%). 1H NMR (DMSO-d6, HMDSO), δ: 6.44 (1H, d, J=16.0 Hz); 7.33-8.11(10H, m); 10.40 (1H, s).

Workup

  1. customMethanol was evaporated
  2. additionthe residue was treated with hydrochloric acid to pH 4
  3. filtrationThe resulting precipitate was filtered off
  4. washwashed with water (3×20 ml)
  5. customdried

Sources & evidence

ORD record
ord-af763cfad0ac44539fc132a2bc33201b
Source dataset
uspto-grants-2009_08
Patent number
US07569724B2

Reaction notes

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