Nitric Acid → HCID 22008421, compound

HRID 321951Notes

Reaction equation

HRID 321951 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:14]2[CH:15]=[C:16]([OH:19])[CH:17]=[CH:18][C:13]=2[CH2:12][CH2:11][N:10]([CH3:20])[CH2:9]1.[N+:21]([O-])([OH:23])=[O:22]>C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:14]2[CH:15]=[C:16]([OH:19])[C:17]([N+:21]([O-:23])=[O:22])=[CH:18][C:13]=2[CH2:12][CH2:11][N:10]([CH3:20])[CH2:9]1

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 22008415HCID 22008415, compound

Product 1

HCID 22008421HCID 22008421, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

5.0 g 5-(2-fluorophenyl)-7-hydroxy-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine was dissolved in 90 ml of a mixture of acetic acid and cooled in ice-water bath 0° C. Under stirring was added 1.7 ml fuming nitric acid and the mixture was stirred in the cold for 1 h. The reaction mixture was neutralized (pH 7.9) and the precipitate was extracted with ethyl acetate, dried and evaporated. After column chromatography (kieselgel/CH2Cl2: CH3OH 95:5) was isolated yellow crystals. M.p. 90-94° C. (dec). NMR: C5H 4.61 d; C6H g 41% 6 s and C9H 7.88 s ppm. respectively.

Workup

  1. additionwas added 1.7 ml
  2. stirringthe mixture was stirred in the cold for 1 h
  3. extractionthe precipitate was extracted with ethyl acetate
  4. customdried
  5. customevaporated
  6. customAfter column chromatography (kieselgel/CH2Cl2: CH3OH 95:5) was isolated yellow crystals
  7. customC5H 4.61 d

Sources & evidence

ORD record
ord-5f27c9ba6d9c493b80416be673a4d2c7
Source dataset
uspto-grants-2001_04
Patent number
US06211173B1

Reaction notes

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