phenyl 2-(8-fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate → phenyl 2-(6-amino-8-fluoro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate

HRID 1922464Notes

Reaction equation

HRID 1922464 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:25]([O-])=O)[CH:5]=[C:6]2[C:11]=1[N:10]([CH2:12][CH2:13][N:14]([CH3:24])[C:15](=[O:23])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][CH2:8][CH2:7]2.[H][H]>[Pd]>[NH2:25][C:4]1[CH:5]=[C:6]2[C:11](=[C:2]([F:1])[CH:3]=1)[N:10]([CH2:12][CH2:13][N:14]([CH3:24])[C:15](=[O:23])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 59807154phenyl 2-(8-fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamateHCID 178418361HCID 178418361, compound

Product 1

HCID 59807114phenyl 2-(6-amino-8-fluoro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamateYield 87.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a stirred solution of phenyl 2-(8-fluoro-6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate (560 mg, 1.500 mmol) was added palladium on activated carbon, 10 wt % (160 mg, 0.150 mmol). The resulting suspension was stirred at room temperature in a balloon pressure atmosphere of hydrogen. After 3 h, most of the starting material was consumed, and the reaction was stopped due to the presence of a minor impurity. The reaction mixture was filtered through a pad of celite, then concentrated to give a brown oil. The residue was dried and use directly in the subsequent reaction. Crude product obtained was phenyl 2-(6-amino-8-fluoro-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate (449 mg, 1.308 mmol, 87% yield). 1 H NMR (DMSO-d6) δ 7.40-7.35 (m, 2H); 7.23-7.17 (m, 1H); 7.10-7.05 (m, 2H); 6.19 (d, J=14 Hz, 1H); 6.06 (s, 1H); 4.85-4.72 (m, 2H); 3.57-3.53 (m, 1H); 3.46-3.42 (m, 1H); 3.13-2.93 (m, 4H); 3.07, 2.95 (2s, 3H); 2.57 (t, J=6.3 Hz, 1H); 1.74-1.65 (m, 2H). ESI-MS (m/z, %): 344 (MH+).

Workup

  1. custommost of the starting material was consumed
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationconcentrated
  4. customto give a brown oil
  5. customThe residue was dried
  6. customuse directly in the subsequent reaction
  7. customCrude product obtained

Sources & evidence

ORD record
ord-5641eceee36b4d70a2978283f1cb5d8f
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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