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

HRID 1922402ノート

反応式

HRID 1922402 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d18c68375ca8413b9d8ea617ee0e56e6
出典データセット
uspto-grants-2012_05
特許番号
US08173813B2

反応ノート

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