Water → 6-Bromo-N'-(4-methyloxan-4-yl)quinoline-3,4-diamine

HRID 1486940

反応式

HRID 1486940 の反応式
O.[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([N+:13]([O-])=O)=[C:6]2[NH:16][C:17]1([CH3:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.Cl.N>CCO.[Fe]>[Br:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([NH2:13])=[C:6]2[NH:16][C:17]1([CH3:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

参加物

6

反応物 3

HCID 962WaterHCID 12820921Azane;hydrochlorideHCID 118498742HCID 118498742、化合物

生成物 1

HCID 1162308926-Bromo-N'-(4-methyloxan-4-yl)quinoline-3,4-diamine収率 87%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 702Ethanol溶媒

反応条件

温度
105 °C

実験手順

Water (8.35 mL) was added to a stirred mixture of 6-bromo-N-(4-methyloxan-4-yl)-3-nitroquinolin-4-amine (1.07 g, 2.92 mmol), iron (0.979 g, 17.53 mmol) and ammonia hydrochloride (0.109 g, 2.05 mmol) in EtOH (50.1 mL) and the resulting slurry heated to 105° C. for 2 h. The reaction was filtered warm through a pad of celite, washing with MeOH, and the filtrate evaporated to dryness. The crude solid was dissolved in DCM (10 mL) and washed with a sat. aqueous solution of NaHCO3 (10 mL) and sat. brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford the desired material (0.850 g, 87%) as a pale orange solid. This was used without further purification. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 1.19 (3H, s), 1.51 (2H, d), 1.76 (2H, td), 3.43 (2H, td), 3.73 (2H, dt), 4.15 (1H, s), 5.45 (2H, s), 7.39 (1H, dd), 7.67 (1H, d), 8.22 (1H, d), 8.51 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=336, 338.

後処理

  1. filtrationThe reaction was filtered
  2. temperaturewarm through a pad of celite
  3. washwashing with MeOH
  4. customthe filtrate evaporated to dryness
  5. dissolutionThe crude solid was dissolved in DCM (10 mL)
  6. washwashed with a sat. aqueous solution of NaHCO3 (10 mL) and sat. brine (10 mL)
  7. dry with materialThe organic layer was dried over MgSO4
  8. filtrationfiltered
  9. customevaporated

出典と根拠

ORDレコード
ord-d5cff58c8135479ca6b5f9d995c6a5e3
出典データセット
uspto-grants-2016_08
特許番号
US09428503B2

関連ノート

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