HCID 57343393, compound → HCID 67492661, compound

HRID 1922498Notes

Reaction equation

HRID 1922498 reaction equation
[CH3:1][N:2]([CH2:12][CH2:13][CH2:14][N:15]1[C:24]2[C:19](=[CH:20][C:21]([N+:25]([O-])=O)=[CH:22][CH:23]=2)[CH2:18][CH2:17][CH2:16]1)[C:3](=[O:11])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C1COCC1.C(O)C.[Pd]>[NH2:25][C:21]1[CH:20]=[C:19]2[C:24](=[CH:23][CH:22]=1)[N:15]([CH2:14][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)[CH2:16][CH2:17][CH2:18]2

Participants

5

Reactant 1

HCID 57343393HCID 57343393, compound

Product 1

HCID 67492661HCID 67492661, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of phenyl methyl(3-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)propyl)carbamate (1.02 g, 2.76 mmol) in THF (15.00 ml) and ethanol (15 ml) was added palladium 10 wt. % on activated carbon (0.294 g, 0.276 mmol). The reaction mixture was stirred under an atmosphere of hydrogen (balloon pressure) for 3 h. The mixture was then filtered through celite and concentrated, giving a dark oil. The crude product (phenyl 3-(6-amino-3,4-dihydroquinolin-1(2H)-yl)propyl(methyl)carbamate (830 mg, 2.445 mmol, 89% yield)) was used directly in the subsequent reaction. ESI-MS (m/z, %) 340 (MH+, 100).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. concentrationconcentrated
  3. customgiving a dark oil

Sources & evidence

ORD record
ord-e4cb3fb3b0e142db989e9ed3d828f227
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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