Water → HCID 66676507, compound

HRID 423286Notes

Reaction equation

HRID 423286 reaction equation
[CH2:1]([O:8][C:9](=[O:27])[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[C:15]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[Cl-].[NH4+]>C1COCC1.C(O)C.[Fe]>[CH2:1]([O:8][C:9](=[O:27])[CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([C:22](=[O:26])[N:23]([CH3:24])[CH3:25])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 66676906HCID 66676906, compound

Product 1

HCID 66676507HCID 66676507, compoundYield 89.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a mixed solution of 4-(3-dimethylcarbamoyl-4-nitrophenyl)butanoic acid benzyl ester (1.39 g) in THF (5 mL), ethanol (15 mL), and water (5 mL) was added ammonium chloride (1.0 g). After heating to 100° C., iron (838 mg) was added thereto in twice. The mixture was further heated for 1.5 hours under reflux, allowed to stand for cooling down to room temperature, and filtered through a Celite pad. The filtrate was concentrated in vacuo. The residue was diluted with ethyl acetate, washed successively with saturated sodium bicarbonate, water, and saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound (1.14 g).

Workup

  1. temperatureThe mixture was further heated for 1.5 hours
  2. temperatureunder reflux
  3. temperaturefor cooling down to room temperature
  4. filtrationfiltered through a Celite pad
  5. concentrationThe filtrate was concentrated in vacuo
  6. additionThe residue was diluted with ethyl acetate
  7. washwashed successively with saturated sodium bicarbonate, water, and saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-fd8d9c0c45b44d838d6537354556b755
Source dataset
uspto-grants-2012_01
Patent number
US08101774B2

Reaction notes

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