Ethanol → HCID 19092349, compound

HRID 257768Notes

Reaction equation

HRID 257768 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH:18]=[C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)=[O:8])=[C:5]([N+:28]([O-])=O)[CH:4]=1.[Sn](Cl)Cl.C(O)C.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[NH2:28][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:27]=[CH:26][C:6]=1[C:7]([NH:9][CH2:10][CH2:11][CH2:12][CH2:13][N:14]1[CH2:15][CH:16]=[C:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:18][CH2:19]1)=[O:8]

Participants

6

Reactant 4

HCID 702EthanolHCID 24479Stannous ChlorideHCID 516892Sodium BicarbonateHCID 19092297HCID 19092297, compound

Product 1

HCID 19092349HCID 19092349, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 4-methoxy-2-nitro-N-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]benzamide (1 g), tin(II) chloride (1.39 g) and ethanol (20 ml) was stirred under reflux for 0.5 hour. After cooling, sat. sodium bicarbonate solution was added and the mixture was diluted with chloroform (50 ml). A chloroform layer was separated, washed in turn with water and brine, dried over magnesium sulfate and evaporated. Crude residue (0.93 g) was chromatographed on a silica gel [13 g, chloroform and methanol (50:1-20:1, V/V) as an eluent] to give 2-Amino-4-methoxy-N-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]benzamide (0.54 g).

Workup

  1. temperatureunder reflux for 0.5 hour
  2. temperatureAfter cooling
  3. customA chloroform layer was separated
  4. washwashed in turn with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customCrude residue (0.93 g) was chromatographed on a silica gel [13 g, chloroform and methanol (50:1-20:1, V/V) as an eluent]

Sources & evidence

ORD record
ord-a82102bfc0814937bc3d210ca15913b5
Source dataset
uspto-grants-1993_11
Patent number
US05264438

Reaction notes

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