Formic Acid → HCID 13207879, compound

HRID 918246Notes

Reaction equation

HRID 918246 reaction equation
[C:1]12([CH2:11][N:12]3[C:21]4[C:16](=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[CH:19][CH:20]=4)[CH:15]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[NH:14][C:13]3=[O:31])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[Mn]([O-])(=O)(=O)=O.[K+].C(O)=O>O1CCOCC1.O>[C:1]12([CH2:11][N:12]3[C:21]4[C:16](=[CH:17][C:18]([N+:22]([O-:24])=[O:23])=[CH:19][CH:20]=4)[C:15]([C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[N:14][C:13]3=[O:31])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 3

HCID 284Formic AcidHCID 516875Potassium PermanganateHCID 21521517HCID 21521517, compound

Product 1

HCID 13207879HCID 13207879, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3.8 g of 1-(1-adamantylmethyl)-4-phenyl-6-nitro-3,4-dihydro-2(1H)-quinazolinone in 70 ml of dioxane was added a suspension of 1.5 g of potassium permanganate in 10 ml of water and the mixture was stirred at room temperature for 3 hours. Then, 7 ml of formic acid was added and stirring was continued for 30 minutes. The brown precipitate was filtered off and the filtrate was diluted with water. The resulting mixture was extracted with chloroform. The chloroform extract was washed, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was crystallized from a mixture of ethanol and chloroform to give 1-(1-adamantylmethyl)-4-phenyl-6-nitro-2(1H)-quinazolinone, m.p. 228°- 231°C.

Workup

  1. stirringstirring
  2. waitwas continued for 30 minutes
  3. filtrationThe brown precipitate was filtered off
  4. additionthe filtrate was diluted with water
  5. extractionThe resulting mixture was extracted with chloroform
  6. extractionThe chloroform extract
  7. washwas washed
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized from a mixture of ethanol and chloroform

Sources & evidence

ORD record
ord-8ccdf468acf8417db915704dd1c23c63
Source dataset
uspto-grants-1976_07
Patent number
US03970654

Reaction notes

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