Dichloromethane → 1-(4-Carbomethoxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester

HRID 435461Notes

Reaction equation

HRID 435461 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6]1)=[O:4].[C:15]([CH2:19][CH2:20][CH:21]([CH3:25])[C:22](Cl)=[O:23])([O:17][CH3:18])=[O:16].C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O>[CH3:1][O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:22](=[O:23])[CH:21]([CH3:25])[CH2:20][CH2:19][C:15]([O:17][CH3:18])=[O:16])=[O:4]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 2736972Methyl 1,2,3,4-tetrahydroquinoline-2-carboxylateHCID 13192898Methyl 5-chloro-4-methyl-5-oxopentanoate

Product 1

HCID 131928991-(4-Carbomethoxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 1.0 g of 1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester (Ber. 61,2377), 0.87 g of 4-carbomethoxy-2-methylbutanoyl chloride, 1.44 g of powdered potassium carbonate and 20 ml of methylene chloride is stirred at room temperature overnight. It is cooled with ice, and 50 ml of water are added. The organic layer is separated, washed with N-hydrochloric acid and water, dried and evaporated, to yield the 1-(4-carbomethoxy-2-methylbutanoyl)-1,2,3,4-tetrahydroquinoline-2-carboxylic acid methyl ester, showing NMR-peaks at 0.85, 1.25, 3.35, 3.65 and 3.75 ppm.

Workup

  1. additionare added
  2. customThe organic layer is separated
  3. washwashed with N-hydrochloric acid and water
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-624f9efadedf425586d828304aa9291a
Source dataset
uspto-grants-1983_08
Patent number
US04401818

Reaction notes

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