Phenyl chloroformate → Phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamate

HRID 1922402Notes

Reaction equation

HRID 1922402 reaction equation
[CH3:1][N:2](C)[CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1.[C:19]1([O:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl>[CH3:1][N:2]([CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[CH:10][C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1)[C:26](=[O:27])[O:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 59807155N,N-Dimethyl-2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine

Product 1

HCID 57343232Phenyl methyl(2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethyl)carbamateYield 85.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N,N-dimethyl-2-(6-nitro-3,4-dihydroquinolin-1(2H)-yl)ethanamine (500 mg, 2.01 mmol) in 10 mL CH2Cl2 was treated dropwise with phenylchloroformate (378 μL, 3.01 mmol). The reaction was stirred at room temperature for 17 hours then partitioned between CH2Cl2 100 mL and 1N NaOH (20 mL). After extraction, the organic layer was separated, dried over Na2SO4, filtered and concentrated to give a yellow residue. This residue was subjected to flash chromatography on silica gel using 20% EtOAc/CH2Cl2 to give a yellow residue (610 mg, 85.4%). 1H-NMR (CDCl3) δ 7.99-7.92 (m, 1H), 7.87 (d, J=2.1 Hz, 1H), 7.39-7.33 (m, 2H), 7.23-7.19 (m, 1H), 7.06-7.01 (m, 2H), 6.69 (m, 1H), 3.67-3.52 (m, 4H), 3.48 (t, J=5.7 Hz, 2H), 3.14 and 3.07 (2×s, 3H), 2.79 (t, J=6.3 Hz, 2H), 1.99-1.96 (m, 2H). MS (ESI): 356.2 (M+1).

Workup

  1. customthen partitioned between CH2Cl2 100 mL and 1N NaOH (20 mL)
  2. extractionAfter extraction
  3. customthe organic layer was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow residue

Sources & evidence

ORD record
ord-d18c68375ca8413b9d8ea617ee0e56e6
Source dataset
uspto-grants-2012_05
Patent number
US08173813B2

Reaction notes

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