Ethanol → HCID 23130242, compound

HRID 2114170Notes

Reaction equation

HRID 2114170 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([F:23])=[CH:11][C:12]([N+:20]([O-])=O)=[C:13]([CH:19]=1)[C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.O.[Cl-].[NH4+]>C1COCC1>[NH2:20][C:12]1[CH:11]=[C:10]([F:23])[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:19][C:13]=1[C:14]([N:16]([CH3:18])[CH3:17])=[O:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 23130305HCID 23130305, compound

Product 1

HCID 23130242HCID 23130242, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-benzyloxy-4-fluoro-N,N-dimethyl-2-nitrobenzamide (1.06 g) in THF (3 mL) were added ethanol (12 mL) and water (1.5 mL), and to the solution were added ammonium chloride (893 mg) and reduced iron (933 mg). The resultant mixture was heated under reflux for 2 hours, allowed to stand for cooling to room temperature, and filtered through a Celite. The filtrate was concentrated and the residue was diluted with ethyl acetate. The extract was washed with successively with saturated aqueous sodium bicarbonate, water, and saturated brine, dried over sodium sulfate, and concentrated to give 2-amino-5-benzyloxy-4-fluoro-N,N-dimethylbenzamide (984 mg) as a crude product.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationfiltered through a Celite
  3. concentrationThe filtrate was concentrated
  4. additionthe residue was diluted with ethyl acetate
  5. washThe extract was washed with successively with saturated aqueous sodium bicarbonate, water, and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-672345b8164c4fc496ac879ffcafa502
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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