HCID 57470253, compound → tert-Butyl 7-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1915372Notes

Reaction equation

HRID 1915372 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([N+:18]([O-])=O)[CH:16]=2)[C:11]([CH3:22])([CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[NH2:18][C:15]1[CH:16]=[C:17]2[C:12]([C:11]([CH3:22])([CH3:21])[CH2:10][CH2:9][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 57470253HCID 57470253, compound

Product 1

HCID 57354996tert-Butyl 7-amino-4,4-dimethyl-3,4-dihydroquinoline-1(2H)-carboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4,4-dimethyl-7-nitro-3,4-dihydro-2H-quinoline-1 carboxylic acid tert-butyl ester (8.3 g, 0.03 mol) and Pd—C (0.5 g) in methanol (100 mL) was stirred under H2 (1 atm) at room temperature overnight. The catalyst was filtered off and the filtrate was concentrated. The residue was washed with petroleum ether to give tert-butyl 7-amino-3,4-dihydro-4,4-dimethylquinoline-1(2H)-carboxylate (DC-3) (7.2 g, 95%). 1H NMR (CDCl3) δ 7.11-7.04 (m, 2H), 6.45-6.38 (m, 1H), 3.71-3.67 (m, 2H), 3.50-3.28 (m, 2H), 1.71-1.67 (m, 2H), 1.51 (s, 9H), 1.24 (s, 6H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. washThe residue was washed with petroleum ether

Sources & evidence

ORD record
ord-4fd96050adad47d8805717e63ffd7bc4
Source dataset
uspto-grants-2013_12
Patent number
US08614327B2

Reaction notes

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