Hydrochloric Acid → Methyl 4-(4'-amino-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate

HRID 30834

Reaction equation

HRID 30834 reaction equation
C([NH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:25])[CH2:17][C:18]([CH3:24])([CH3:23])[C:19]([O:21][CH3:22])=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)=O.Cl>CO>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=[O:25])[CH2:17][C:18]([CH3:23])([CH3:24])[C:19]([O:21][CH3:22])=[O:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21985799Methyl 4-[4'-(formylamino)-1,1'-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate

Product 1

HCID 21985743Methyl 4-(4'-amino-1,1'-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoateYield 95.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of methyl 4-[4′-(formylamino)-1,1′-biphenyl-4-yl]-2,2-dimethyl-4-oxobutanoate (2.40 g, 7.07 mmol) in 20 mL methanol, was added 7 mL concentrated hydrochloric acid at below rt. The reaction mixture was stirred at rt overnight. The mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution was slowly added until pH>8.0. The aqueous layer was then extracted with methylene chloride (2×25 mL), and the combined organic layer was dried over sodium sulfate. The mixture was concentrated under reduced pressure to afford methyl 4-(4′-amino-1,1′-biphenyl-4-yl)-2,2-dimethyl-4-oxobutanoate as a light red solid (2.1 g, 95%). 1H NMR (CDCl3) δ 7.96 (d, J=9Hz, 2H), 7.60 (d, J=9Hz, 2H), 7.46 (d, J=9Hz, 2H), 6.76 (d, J=9Hz, 2H), 3.85 (br s, 2H), 3.69 (s, 3H), 3.32 (s, 2H), 1.35 (s, 6H); ESI-MS m/z 312.4 (MH+); HRMS m/z calcd for MH+ 312.1594, found 312.1597.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure and saturated aqueous sodium bicarbonate solution
  2. additionwas slowly added until pH>8.0
  3. extractionThe aqueous layer was then extracted with methylene chloride (2×25 mL)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. concentrationThe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-feed16e613f34d76a7aedcebda9a0d7e
Source dataset
uspto-grants-2008_09
Patent number
US07423156B2

Linked notes

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