Ethyl 4,4,4-trifluoroacetoacetate → 2-Hydroxyquinoline

HRID 1861738Notes

Reaction equation

HRID 1861738 reaction equation
N[C:2]1[C:11](C)=[C:10]2[C:5]([C:6](C)=[CH:7][C:8](C)(C)[NH:9]2)=[CH:4][CH:3]=1.FC(F)(F)C(=O)CC(OCC)=[O:21]>>[NH:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:2][CH:11]=2)[CH:6]=[CH:7][C:8]1=[O:21]

Participants

3

Reactant 2

HCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 10631958HCID 10631958, compound

Product 1

HCID 60382-HydroxyquinolineYield 105.4%

Procedure

This compound was prepared in a manner similar to that described for Compound 102 (EXAMPLE 2) with 7-amino-1,2-dihydro-2,2,4,8-tetramethylquinoline (100 mg, 0.49 mmol) and ethyl 4,4,4-trifluoroacetoacetate (107 mL, 0.73 mmol, 1.5 equiv), affording 75 mg (47%) of the desired 2-quinolone as a fluorescent-yellow solid. Data for 1,2-dihydro-2,2,4,10-tetramethyl-6-trifluoromethyl-8-pyridono[5,6-f]quinoline: 1H NMR (400 MHz, CDCl3) 9.23 (br s, 1H, CONH), 7.37 (s, 1H, 5-H), 6.67 (s, 1H, 7-H), 5.45 (s, 1H, 3-H), 4.14 [br s, 1H, (CH3)2CNH], 2.12 (s, 3H, 10-CH3), 2.04 (d, 3H, J=1.1 Hz, 4-CH3), 1.37 [s, 6H, 2-(CH3)2].

Workup

  1. customThis compound was prepared in a manner similar to

Sources & evidence

ORD record
ord-423083ecc3df4bf099e262c8debecdbb
Source dataset
uspto-grants-2003_03
Patent number
US06534516B1

Reaction notes

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