Isobutyryl chloride → Methyl-2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 2045545Notes

Reaction equation

HRID 2045545 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:17]([CH3:19])([CH3:18])[CH2:16][C:15]3[C:10](=[CH:11][CH:12]=[C:13]([C:20]([O:22][CH3:23])=[O:21])[CH:14]=3)[NH:9]2)=[CH:4][C:3]=1[N+:24]([O-])=O.C(N(CC)C(C)C)(C)C.[C:36](Cl)(=[O:40])[CH:37]([CH3:39])[CH3:38]>ClCCl>[CH3:23][O:22][C:20]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:24][C:36](=[O:40])[CH:37]([CH3:39])[CH3:38])[CH:4]=1)[C:17]([CH3:19])([CH3:18])[CH2:16]2)=[O:21]

Participants

5

Reactant 3

HCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 67442620Methyl 2-(4-fluoro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 67441749Methyl-2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(4-fluoro-3-nitrophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (150 mg, 0.46 mmol) and N,N-diisopropylethylamine (0.15 mL, 0.91 mmol) in dichloromethane (10 mL) was added isobutyryl chloride (0.053 mL, 0.50 mmol) via syringe with ice cooling. The resultant mixture was stirred for an additional 20 h. The solvent was removed in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=3:1) to afford 183 mg of methyl-2-(4-fluoro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate. Yield: 97%.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column chromatography (petroleum ether:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-af0739ea156f4ecbae24a976ec2d1cc9
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

Loading…