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

HRID 401376Notes

Reaction equation

HRID 401376 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-148eb40ada1a4053a2837eafc4564838
Source dataset
uspto-grants-2014_06
Patent number
US08741925B2

Reaction notes

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