Hydrochloric Acid → N-biphenyl-4-yl-N-methyl-malonamic acid

HRID 1665680Notes

Reaction equation

HRID 1665680 reaction equation
O[Li].O.C([O:6][C:7](=[O:25])[CH2:8][C:9]([N:11]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)[CH3:12])=[O:10])C.C1COCC1.Cl>CO.O>[C:16]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:17]=[CH:18][C:13]([N:11]([CH3:12])[C:9](=[O:10])[CH2:8][C:7]([OH:25])=[O:6])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 57875797N-biphenyl-4-yl-N-methyl-malonamic acid ethyl ester

Product 1

HCID 57875814N-biphenyl-4-yl-N-methyl-malonamic acidYield 95.24%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

LiOH.H2O (25 mg, 0.58 mmol) was added to a solution of N-biphenyl-4-yl-N-methyl-malonamic acid ethyl ester (116 mg, 0.39 mmol) in a mixture of Methanol (0.6 mL), THF (1.5 mL) and H2O (0.4 mL). The resulting mixture was stirred at ambient temperature for 2 hrs. The reaction mixture was concentrated to get a residue. The residue was diluted with water, acidified with conc. HCl. The precipitate was collected and dried to afford 100 mg (95.24%) of N-biphenyl-4-yl-N-methyl-malonamic acid

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto get a residue
  3. customThe precipitate was collected
  4. customdried

Sources & evidence

ORD record
ord-b5324be6e4e94f528d4478ed50d7bc3b
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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