Ethanol → HCID 66711269, compound

HRID 1262341Notes

Reaction equation

HRID 1262341 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:13][CH2:14][N:15]([CH2:18][C:19]([NH2:21])=[O:20])[CH2:16][CH:17]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O.[Cl-].[NH4+].C(O)C.O>[Fe]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:12]2[CH2:17][CH2:16][N:15]([CH2:18][C:19]([NH2:21])=[O:20])[CH2:14][CH:13]=2)=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 56945961HCID 56945961, compound

Product 1

HCID 66711269HCID 66711269, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 2-[4-(3-Methoxy-4-nitro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetamide (240 mg, 0.82 mmol), iron (138 mg, 2.47 mmol), ammonium chloride (22.0 mg, 0.412 mmol) in ethanol (7 mL, 100 mmol) and water (3 mL, 200 mmol) was heated at 80° C. After 3 h, MS showed product with no SM. The mixture was cooled, solvent was evaporated and was diluted with aq. Na2CO3 solution and EtOAc. The mixture was filtered through a pad of celite, extracted from EtOAc, combined organic was washed with brine. After drying, the solvent was evaporated to give the product, 2-[4-(4-Amino-3-methoxy-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-acetamide, as a foam (195 mg, 91%). The product was taken to the next step without further purification. MS: 262 (M+H).

Workup

  1. temperatureThe mixture was cooled
  2. customsolvent was evaporated
  3. additionwas diluted with aq. Na2CO3 solution and EtOAc
  4. filtrationThe mixture was filtered through a pad of celite
  5. extractionextracted from EtOAc
  6. washcombined organic was washed with brine
  7. customAfter drying
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9ce829b7f99f47a895b28253c8510831
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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