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

HRID 1181362ノート

反応式

HRID 1181362 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-af50e38c158d44a6a6dbe577d9c3cf91
出典データセット
uspto-grants-2007_10
特許番号
US07285557B2

反応ノート

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