Phosphoric Acid → HCID 69055426, compound

HRID 2103070Notes

Reaction equation

HRID 2103070 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:10][C:11]2([C:15]([OH:17])=O)[CH2:14][CH2:13][CH2:12]2)=[C:5]([CH3:18])[C:4]=1[CH3:19].P(=O)(O)(O)O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]2[C:6](=[C:5]([CH3:18])[C:4]=1[CH3:19])[NH:9][CH2:10][C:11]1([CH2:12][CH2:13][CH2:14]1)[C:15]2=[O:17]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 69053921HCID 69053921, compound

Product 1

HCID 69055426HCID 69055426, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
116 °C

Procedure

A solution of 1-((4-methoxy-2,3-dimethylphenylamino)methyl)cyclobutanecarboxylic acid (19 g in toluene (100 mL) was added into phosphoric acid (25 mL). The mixture was heated up in a 116° C. bath and stirred for an hour. The mixture was then cooled down, quenched with ice, and extracted with ethylacetate. The organic phase was then dried and evaporated to dryness. The crude product was passed through a column (Hexane: EtOAc; 10:4) to give 6′-methoxy-7′,8′-dimethyl-1′H-spiro[cyclobutane-1,3′-quinolin]-4′(2′H)-one (15 g) as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ=7.26 (s, 1H), 4.11 (s, 1H), 3.79 (s, 3H), 3.54 (s, 2H), 2.59-2.29 (m, 2H), 2.38 (3H), 2.34 (3H), 2.06-1.82 (4H) ppm. 13C-NMR (75 MHz, CDCl3) δ=196.22, 150.49, 144.93, 133.95, 122.36, 115.05, 104.75, 55.77, 51.45, 46.5, 25.95, 15.06, 12.98, 12.77 ppm.

Workup

  1. temperatureThe mixture was then cooled down
  2. customquenched with ice
  3. extractionextracted with ethylacetate
  4. customThe organic phase was then dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-989e6dc8911c4c56bdfc864bccb65fcc
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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