Water → 6'-methoxy-5',7'-dimethyl-1'H-spiro[cyclobutane-1,2'-quinolin]-4'(3'H)-one

HRID 2103081Notes

Reaction equation

HRID 2103081 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([NH:10][C:11]2([CH2:15][C:16]([OH:18])=O)[CH2:14][CH2:13][CH2:12]2)=[CH:5][C:4]=1[CH3:19].O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([CH3:19])=[C:5]2[C:6](=[CH:7][C:8]=1[CH3:9])[NH:10][C:11]1([CH2:12][CH2:13][CH2:14]1)[CH2:15][C:16]2=[O:18]

Participants

4

Reactant 2

HCID 962WaterHCID 690565892-(1-(4-Methoxy-3,5-dimethylphenylamino)cyclobutyl)acetic acid

Product 1

HCID 690552306'-methoxy-5',7'-dimethyl-1'H-spiro[cyclobutane-1,2'-quinolin]-4'(3'H)-oneYield 165.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(1-(4-methoxy-3,5-dimethylphenylamino)cyclobutyl)acetic acid (650 mg) in 10 mL toluene was added a large excess of polyphosphoric acid. The mixture was refluxed for 30 minutes, water was added, and the solution was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and the solvent was removed by evaporation, giving 6′-methoxy-5′,7′-dimethyl-1′H-spiro[cyclobutane-1,2′-quinolin]-4′(3′H)-one as a yellow solid (1 g). 1H-NMR (300 MHz, CDCl3) δ=6.25 (s, 1H), 2.78 (s, 2H), 2.55 (s, 3H), 2.125-2.38 (m, 5H), 1.95-2.06 (m, 2H), 1.73-1.83 (m, 2H) ppm. MS: m/z 246 (100, M+H)+

Workup

  1. temperatureThe mixture was refluxed for 30 minutes
  2. extractionthe solution was extracted with ethyl acetate (3×20 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-e0e320a273b741e28d299f080be8f849
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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