Lithium hydroxide, monohydrate → N-biphenyl-4-yl-malonamic acid

HRID 1665591Notes

Reaction equation

HRID 1665591 reaction equation
O[Li].O.C([O:6][C:7](=[O:24])[CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)=[O:10])C>CO.C1COCC1.O>[C:15]1([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:16]=[CH:17][C:12]([NH:11][C:9](=[O:10])[CH2:8][C:7]([OH:24])=[O:6])=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 57875823N-biphenyl-4-yl-malonamic acid ethyl ester

Product 1

HCID 55049154N-biphenyl-4-yl-malonamic acidYield 89.5%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

LiOH.H2O (29 mg, 0.7 mmol) was added to a solution of N-biphenyl-4-yl-malonamic acid ethyl ester (100 mg, 0.35 mmol) in methanol (2.1 mL), THF (2.5 mL) and H2O (2.5 mL). The resulting mixture was stirred for 2 hours at room temperature then concentrated. The residue was diluted with water and washed with diethyl ether. The aqueous layer was acidified with concentrated HCl and filtered. The resulting precipitate was dried to afford 80 mg (89%) of N-biphenyl-4-yl-malonamic acid. 1H NMR: (DMSO-d6): δ11.6 (s, 1H), 7.64 (m, 6H), 7.44 (t, 2H), 7.32 (t, 1H), 3.2 (s, 1H).

Workup

  1. concentrationthen concentrated
  2. additionThe residue was diluted with water
  3. washwashed with diethyl ether
  4. filtrationfiltered
  5. customThe resulting precipitate was dried

Sources & evidence

ORD record
ord-cab6376481ae4d0297f862c0e0cf5d0e
Source dataset
uspto-grants-2011_10
Patent number
US08039463B2

Reaction notes

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