Ammonia → HCID 14031661, compound

HRID 1464512Notes

Reaction equation

HRID 1464512 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-2yl)-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-d735c54559984986b98b5e1b18321aab
Source dataset
uspto-grants-1994_04
Patent number
US05304658

Reaction notes

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