Tetrahydrofuran → Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate

HRID 1922412Notes

Reaction equation

HRID 1922412 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][N:14]1[C:23]2[C:18](=[CH:19][C:20]([N+:24]([O-])=O)=[CH:21][CH:22]=2)[CH2:17][CH2:16][C:15]1=[O:27])[C:3](=[O:11])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1COCC1>C(O)C>[NH2:24][C:20]1[CH:19]=[C:18]2[C:23](=[CH:22][CH:21]=1)[N:14]([CH2:13][CH2:12][N:2]([CH3:1])[C:3](=[O:11])[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:15](=[O:27])[CH2:16][CH2:17]2

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 59807118HCID 59807118, compound

Product 1

HCID 59807067Phenyl 2-(6-amino-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Phenyl methyl(2-(6-nitro-2-oxo-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate (1.29 g, 3.49 mmol) was dissolved by stirring in ethanol (40 mL) and THF (30 mL) in a round bottom flask. The solution was stirred under an atmosphere of hydrogen for 6 h at room temperature. When TLC confirmed the reaction was completed, the mixture was filtered through celite, and the filtrate was concentrated. The resulting residue was chromatographed on silica gel eluting with ethyl acetate, giving a white/pink foam. Yield: 990 mg, 84%. 1H NMR (DMSO-d6) δ 7.36 (m, 2H), 7.20 (m, 1H), 7.01 (m, 2H); 6.91 (d, 1H, J=8.4 Hz), 6.43 (m, 2H), 4.87 (s, 2H), 4.11 and 4.03 (2m, 2H), 3.56 and 3.44 (2t, 2H, J=6.0 Hz), 2.99 and 2.87 (2s, 3H), 2.66 (m, 2H), 2.43 (m, 2H); ESI-MS (m/z, %): 362 (MNa+, 35), 340 (MH+, 100), 202 (44).

Workup

  1. filtrationthe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting residue was chromatographed on silica gel eluting with ethyl acetate
  4. customgiving a white/pink foam

Sources & evidence

ORD record
ord-5b7cec2ee51c40029b60e15c1f9b39e8
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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