Ethyl Acetate → Methyl 2-(4-chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

HRID 1801275Notes

Reaction equation

HRID 1801275 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]([CH3:20])([CH3:19])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21]([O:23][CH3:24])=[O:22])[CH:15]=3)[NH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)C(C)C)(C)C.[C:34](Cl)(=[O:38])[CH:35]([CH3:37])[CH3:36].C(OCC)(=O)C>ClCCl>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([CH:9]2[C:18]([CH3:19])([CH3:20])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21]([O:23][CH3:24])=[O:22])[CH:15]=3)[NH:10]2)=[CH:3][C:2]=1[NH:1][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 62325Isobutyryl chlorideHCID 81531DiisopropylethylamineHCID 67441358Methyl 2-(3-amino-4-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 67441325Methyl 2-(4-chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylateYield 109.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-(3-amino-4-chlorophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (182 mg, 0.53 mmol) in dichloromethane (5 mL) was added N,N-diisopropyle thylamine (136 mg, 1.06 mmol) with ice cooling, followed by the addition of isobutyryl chloride (84 mg, 0.8 mmol) in dichloromethane (2 mL) via syringe. The resultant mixture was stirred at room temperature overnight. Thin layer chromatography (petroleum ether: ethyl acetate=10:1) showed the reaction was complete. The mixture was separated by Preparative Thin layer chromatography to afford 240 mg of methyl 2-(4-chloro-3-isobutyramidophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate, which was used in next step without further purification.

Workup

  1. customThe mixture was separated by Preparative Thin layer chromatography

Sources & evidence

ORD record
ord-797ea07a6c764b40a5ec737a8f31aee3
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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