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

HRID 1486940

반응식

HRID 1486940 반응식
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

참가 물질

6

반응물 3

HCID 962WaterHCID 12820921Azane;hydrochlorideHCID 118498742HCID 118498742, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 702Ethanol용매

반응 조건

온도
105 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d5cff58c8135479ca6b5f9d995c6a5e3
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09428503B2

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