Ammonia → HCID 18933561, compound

HRID 1598145Notes

Reaction equation

HRID 1598145 reaction equation
[CH3:1][O:2][C:3]1[CH:27]=[CH:26][C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15](=O)[C:16]2[CH:21]=[CH:20][C:19]3[O:22][CH2:23][O:24][C:18]=3[CH:17]=2)=[O:8])=[CH:5][CH:4]=1.CC(C)=O.C(=O)=O.[NH3:35]>>[OH:8][C:7]1([C:6]2[CH:26]=[CH:27][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:15]([C:16]2[CH:21]=[CH:20][C:19]3[O:22][CH2:23][O:24][C:18]=3[CH:17]=2)=[N:35]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 18522661Acetone cardiceHCID 18933565HCID 18933565, compound

Product 1

HCID 18933561HCID 18933561, compoundYield 90%

Conditions

Temperature
70 °C

Procedure

A bomb was charged 1-(4-methoxybenzoyl)-2-(3,4-methylenedioxybenzoyl)benzene (1.0 g, 2.8 mmol) was cooled to -78° C. (acetone/dry ice bath), and liquid ammonia (20 ml) was added and the vessel was sealed. The reaction was heated at 70° C. reaching a steady pressure of 300 psi for 24 h. The pressure was slowly released after the mixture had cooled to room temperature, and the brown residue was partitioned between ethyl acetate and water. The organic extract was acidified with 3N HCl. The resulting aqueous layer (containing the hydrochloride salt) was washed with ethyl acetate, then basified by treatment with concentrated ammonium hydroxide and extracted with ethyl acetate. The combined organic extract was successively washed with water brine and dried (MgSO4). Removal of the solvent under reduced pressure gave an isomeric mixture of the title compound as a brown foam (0.900 g, 90%).

Workup

  1. additionwas added
  2. customthe vessel was sealed
  3. customfor 24 h
  4. temperaturehad cooled to room temperature
  5. customthe brown residue was partitioned between ethyl acetate and water
  6. extractionThe organic extract
  7. additionThe resulting aqueous layer (containing the hydrochloride salt)
  8. washwas washed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. extractionThe combined organic extract
  11. washwas successively washed with water brine
  12. dry with materialdried (MgSO4)
  13. customRemoval of the solvent under reduced pressure
  14. customgave

Sources & evidence

ORD record
ord-8cc441b27b614e6d81fe9e733d26a846
Source dataset
uspto-grants-1998_04
Patent number
US05736564

Reaction notes

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