Ammonia → HCID 14031661, compound

HRID 1646808Notes

Reaction equation

HRID 1646808 reaction equation
[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18](OC1C=CC([N+]([O-])=O)=CC=1)=[O:19].[NH3:36]>O1CCCC1>[CH3:1][C:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([CH3:10])[C:4](=[O:11])[C:3]=1[CH:12]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([NH2:36])=[O:19]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 19088025HCID 19088025, compound

Product 1

HCID 14031661HCID 14031661, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of p-nitrophenyl 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenyl-heptanate (0.71 g, 1.5 mmoles) in tetrahydrofuran (7 ml) was added concentrated ammonia (1.0 ml) at room temperature and kept stirring for 4 hours. After the reaction was completed, the solvent was evaporated in a reduced pressure. To the residue was added aqueous potassium carbonate and then extracted with ethylacetate. The organic layer was washed with water, dried over magnesium sulfate. Evaporation of the solvent gave 7-(3,5,6-trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanamide (0.46 g, 87%)

Workup

  1. customthe solvent was evaporated in a reduced pressure
  2. additionTo the residue was added aqueous potassium carbonate
  3. extractionextracted with ethylacetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-12c86df19e2848f8829e5a5467c46789
Source dataset
uspto-grants-1993_01
Patent number
US05180742

Reaction notes

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