Ethyl Acetate → 3-(6-(Methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid

HRID 1801255Notes

Reaction equation

HRID 1801255 reaction equation
C([O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:17]2[C:26]([CH3:28])([CH3:27])[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:29]([O:31][CH3:32])=[O:30])[CH:23]=3)[NH:18]2)[CH:14]=[CH:15][CH:16]=1)=[O:10])C1C=CC=CC=1.C(OCC)(=O)C>CO.O1CCCC1.[Pd]>[CH3:32][O:31][C:29]([C:22]1[CH:23]=[C:24]2[C:19](=[CH:20][CH:21]=1)[NH:18][CH:17]([C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[C:9]([OH:10])=[O:8])[C:26]([CH3:28])([CH3:27])[CH2:25]2)=[O:30]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 67441533Methyl 2-(3-(benzyloxycarbonyl)phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate

Product 1

HCID 674419763-(6-(Methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acidYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of methyl 2-(3-(benzyloxycarbonyl)-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylate (10.2 g, 23.7 mmol, 1.0 eq.), 2.04 g Pd/C in methanol/tetrahydrofuran (V/V=1/1, 102 mL) was treated with H2 at room temperature overnight. Thin layer chromatography (petroleum ether: ethyl acetate=3:1) showed the reaction was complete. The mixture was separated by filtration and the filtrate was concentrated in vacuo to give 7.35 g of 3-(6-(methoxycarbonyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinolin-2-yl)benzoic acid as a white solid, yield: 91.2%. MS (ESI+APCI) M+1=340.1.

Workup

  1. additionwas treated with H2 at room temperature overnight
  2. customThe mixture was separated by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6b95ec8714fd460a9e32a9cdb9806f82
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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