Sodium Bicarbonate → Methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoate

HRID 1080777Notes

Reaction equation

HRID 1080777 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:15]2[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:16]=2[S:17][CH:18]=1)[C:6]([O:8][CH3:9])=[O:7].C(=O)(O)[O-].[Na+]>C(O)C>[NH2:23][C:21]1[CH:20]=[CH:19][C:16]2[S:17][CH:18]=[C:14]([CH2:13][C:12]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[O:2][CH3:1])[C:15]=2[CH:22]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 14763112Methyl 3-methoxy4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate

Product 1

HCID 14763113Methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoateYield 54.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Stannous chloride dihydrate (0.38 g.) was added to a stirred solution of (I) (0.12 g.) in ethanol (5 ml.), under an atmosphere of nitrogen. The mixture was heated under reflux for 2 hours. The cooled mixture was basified with saturated aqueous sodium bicarbonate (15 ml.) and extracted with ethyl acetate (2×25 ml.). The extracts were dried (MgSO4) and evaporated. The residual oil was purified by flash chromatography on silica gel (50 ml.), eluting with 3:7 v/v ethyl acetate:hexane to give methyl 4-(5-aminobenzo[b]thien-3-ylmethyl)-3-methoxybenzoate (H) (0.06 g., 54%) as an oil; NMR (80 MHz, DMSO-d6): 3.84 (s, 3H, OCH3), 3.91 (s,3H, OCH3), 4.03(s,2H, CH2 --Ar), 5.0(br s,2H, NH2), 6.80(m,2H), 7.14(m,2H), 7.52(m,3H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate (2×25 ml.)
  4. dry with materialThe extracts were dried (MgSO4)
  5. customevaporated
  6. customThe residual oil was purified by flash chromatography on silica gel (50 ml.)
  7. washeluting with 3:7 v/v ethyl acetate

Sources & evidence

ORD record
ord-62fdf392890443bcb5fd948de48d8de6
Source dataset
uspto-grants-1996_12
Patent number
US05583152

Reaction notes

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