2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide → 6'-hydroxy-7',8'-dimethyl-1'H-spiro[cyclobutane-1,4'-quinolin]-2'(3'H)-one

HRID 2103085Notes

Reaction equation

HRID 2103085 reaction equation
[C:1]1(=[CH:5][C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[C:11]([CH3:17])[C:10]=2[CH3:18])=[O:7])[CH2:4][CH2:3][CH2:2]1>CS(O)(=O)=O>[OH:15][C:12]1[CH:13]=[C:14]2[C:9](=[C:10]([CH3:18])[C:11]=1[CH3:17])[NH:8][C:6](=[O:7])[CH2:5][C:1]12[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 690533272-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide

Product 1

HCID 690541776'-hydroxy-7',8'-dimethyl-1'H-spiro[cyclobutane-1,4'-quinolin]-2'(3'H)-oneYield 53%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

A solution of 2-cyclobutylidene-N-(4-methoxy-2,3-dimethylphenyl)acetamide (5 g) in methane sulfonic acid (20 mL) was refluxed at 120° C. overnight. After cooling down, the solution was poured onto ice. The solid present was collected by filtration and washed with water (×3), giving 6′-hydroxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,4′-quinolin]-2′(3′H)-one (2.5 g) which was used in the next step without further purification. 1H-NMR (300 MHz, CDCl3) δ=6.8 (s, 1H); 3.37 (s, 1H); 2.64 (s, 2H); 2.43 (m, 3H); 2.16 (s, 6H); 2.07 (m, 3H) ppm. MS: (m/z)=232 (100, M+H+).

Workup

  1. temperatureAfter cooling down
  2. additionthe solution was poured onto ice
  3. filtrationThe solid present was collected by filtration
  4. washwashed with water (×3)

Sources & evidence

ORD record
ord-537634aa284a4e6486a43741887f96c7
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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