Stannous chloride dihydrate → 2-amino-4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}benzamide

HRID 1181362노트

반응식

HRID 1181362 반응식
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:11]([O:23][CH3:24])[CH:10]=2)=[O:7])=[C:4]([N+:27]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl>C(O)C>[NH2:27][C:4]1[CH:3]=[C:2]([Cl:1])[CH:26]=[CH:25][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)=[C:11]([O:23][CH3:24])[CH:10]=1)=[O:7]

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 589808694-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamide

생성물 1

HCID 589808752-amino-4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}benzamide수율 97%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 4-chloro-N-{3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl}-2-nitrobenzamide (11.9 mmol, 5.0 g) in ethanol was added tin(II) chloride dihydrate (35.8 mmol, 8.1 g). The resulting mixture was heated to reflux for 4 h and then concentrated by rotary evaporation. The residue was dissolved in ethyl acetate and was washed with potassium sodium tartrate tetrahydrate solution repeatedly. The crude product was first extracted with 2N HCl, then made basic by adding NaOH with ice cooling. The combined basic aqueous solution was extracted with DCM. The organic extraction was washed with brine, dried and concentrated giving the product (4.5 g, 97%). 1H NMR (DMSO-D6): δ 1.67 (4H, m), 2.48 (4H, m), 2.81 (2H, t, J=5.8 Hz), 3.75 (3H, s), 4.10 (2H, t, J=5.8 Hz), 7.02 (1H, d, J=6.2 Hz), 7.10 (1H, d, J=8.6 Hz), 7.16 (1H, s), 7.62 (1H, d, J=8.6 Hz), 7.80 (1H, s), 8.17 (1H, d, 8.6 Hz), 8.35 (1H, s). LCMS m/z=390 (m+H+).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationconcentrated by rotary evaporation
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwas washed with potassium sodium tartrate tetrahydrate solution repeatedly
  6. extractionThe crude product was first extracted with 2N HCl
  7. additionby adding NaOH with ice cooling
  8. extractionThe combined basic aqueous solution was extracted with DCM
  9. extractionThe organic extraction
  10. washwas washed with brine
  11. customdried
  12. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af50e38c158d44a6a6dbe577d9c3cf91
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07285557B2

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