Ethyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate → Ethyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylate

HRID 570386Notes

Reaction equation

HRID 570386 reaction equation
[CH3:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:23]([O-])=O)[CH:8]=2)[N:3]=1>CCOC(C)=O.[Pd]>[NH2:23][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][CH2:15][CH3:16])=[O:13])=[C:10]2[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 966460Ethyl 2-methyl-6-nitro-4-phenylquinoline-3-carboxylate

Product 1

HCID 68294637Ethyl 6-amino-2-methyl-4-phenylquinoline-3-carboxylateYield 146.6%

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-8a5e847f7edf423bb7eb8249f9bc4054
Source dataset
uspto-grants-2015_05
Patent number
US09023848B2

Reaction notes

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