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Water → N-biphenyl-4-yl-2-methyl-malonamic acid

HRID 1665676
Notes
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Reaction equation

HRID 1665676 reaction equation
O[Li].O.C[O:5][C:6](=[O:24])[CH:7]([CH3:23])[C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][CH:12]=1)=[O:9].C1COCC1.O>CO>[C:14]1([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:15]=[CH:16][C:11]([NH:10][C:8](=[O:9])[CH:7]([CH3:23])[C:6]([OH:24])=[O:5])=[CH:12][CH:13]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57875815N-biphenyl-4-yl-2-Methyl-malonamic acid methyl ester

Product 1

HCID 57875794N-biphenyl-4-yl-2-methyl-malonamic acidYield 83.2%

Reagents, catalysts & solvents 1

HCID 887
Methanol
Solvent

Procedure

LiOH.H2O (73 mg, 1.7 mmol) was added to a solution of N-biphenyl-4-yl-2-methyl-malonamic acid methyl ester (330 mg, 1.16 mmol) in a mixture of methanol (1.75 mL), THF (10 mL) and H2O (1 mL). The resulting mixture was stirred for 2 hours at ambient temperature then concentrated. The residue was diluted with water, acidified with conc. HCl. The resulting precipitate was isolated by filtration and dried to afford 260 mg (83%) of N-biphenyl-4-yl-2-methyl-malonamic acid.

Workup

  1. concentrationthen concentrated
  2. additionThe residue was diluted with water
  3. customThe resulting precipitate was isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-14528dbd49954d23b5ebeb8de75307a8
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08039463B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes