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

HRID 1181362Notes

Reaction equation

HRID 1181362 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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+).

Workup

  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

Sources & evidence

ORD record
ord-af50e38c158d44a6a6dbe577d9c3cf91
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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