tert-Butyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate → tert-Butyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate

HRID 570378Notes

Reaction equation

HRID 570378 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[C:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:25]([O-])=O)[CH:8]=2)[N:3]=1>CCOC(C)=O.[Pd]>[NH2:25][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[C:11]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])=[C:10]2[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 86713556tert-Butyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate

Product 1

HCID 86713557tert-Butyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylateYield 134.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product of Step 1 (1.05 g, 3.25 mmol) and 10% Pd/C (0.222 g, 32.5) in EtOAc was degassed under reduced pressure and saturated with H2 gas. The resulting mixture was stirred overnight under H2 balloon at room temperature, filtered through Celite bed and filtrate evaporated to dryness to give product as an yellowish solid (1.46 g, 98%), which was used in next step without further purification. 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.9 Hz, 1H), 7.43-7.48(m, 3H), 7.27-7.34(m, 2H), 7.10 (dd, J=2.5, 8.9 Hz, 1H), 6.55(d, J=2.5 Hz, 1H), 3.79(broad s, 2H), 2.69(s, 3H), 1.2(s, 9H).

Workup

  1. customwas degassed under reduced pressure and saturated with H2 gas
  2. filtrationfiltered through Celite bed and filtrate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-f9dbd47cee7e4844b0170179ab7b4eb8
Source dataset
uspto-grants-2015_05
Patent number
US09023848B2

Reaction notes

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