Ethyl Acetate → Methyl 7,7-dimethyl-9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylate

HRID 521400Notes

Reaction equation

HRID 521400 reaction equation
Br[C:2]1[C:15]2[NH:14][C:13]3[CH2:12][CH2:11][C:10]([CH3:17])([CH3:16])[CH2:9][C:8]=3[C:7](=[O:18])[C:6]=2[C:5]([C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=1.C(OCC)(=O)C>[Pd].CO>[CH3:16][C:10]1([CH3:17])[CH2:9][C:8]2[C:7](=[O:18])[C:6]3[C:5]([C:19]([O:21][CH3:22])=[O:20])=[CH:4][CH:3]=[CH:2][C:15]=3[NH:14][C:13]=2[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 89655891Methyl 4-bromo-7,7-dimethyl-9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylate

Product 1

HCID 89655909Methyl 7,7-dimethyl-9-oxo-5,6,7,8,9,10-hexahydroacridine-1-carboxylateYield 105.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A mixture of methyl 4-bromo-7,7-dimethyl-9-oxo-5,6,7,8,9,10-hexahydro-acridine-1-carboxylate (4.0 g, 11 mmol), ethyl acetate (300 mL), Pd/C (5% Pd on carbon, 50% water, 4.0 g) was stirred at room temperature under an atmosphere of hydrogen for 6 hours. Methanol (100 mL) and Pd/C (5% Pd on carbon, 50% water, 8.0 g) was added to the mixture and stirred for another 1 hour. The mixture was filtered through celite and the filtrate was concentrated to give the desired product (3.3 g, crude) which was used to next step without further purification. 1H NMR (DMSO-d6) δ 11.70-11.72 (m, 1H), 7.60-7.63 (m, 2H), 7.13-7.14 (m, 1H), 3.79 (s, 3H), 2.76-2.77 (m, 2H), 2.23 (s, 2H), 1.55-1.57 (m, 2H), and 0.97 (s, 6H). MS (ESI) m/e [M+1]+286.

Workup

  1. stirringstirred for another 1 hour
  2. filtrationThe mixture was filtered through celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-6cab9078569e42fda8bd494be7f957a3
Source dataset
uspto-grants-2016_05
Patent number
US09328111B2

Reaction notes

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