Butyl nitrite → HCID 178526323, compound

HRID 2081925Notes

Reaction equation

HRID 2081925 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:23]=[CH:22][C:7]2=[C:8]3[C:17](=[CH:18][CH:19]=[C:6]2[CH:5]=1)[C:16](=[O:20])[C:15]1[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:9]3=[O:21].CCCC[O:28][N:29]=O>O.C(O)CCC>[OH:3][C:4]1[CH:23]=[CH:22][C:7]2=[C:8]3[C:17](=[CH:18][CH:19]=[C:6]2[C:5]=1[N:29]=[O:28])[C:16](=[O:20])[C:15]1[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=1)[C:9]3=[O:21]

Participants

6

Reactant 3

HCID 10996Butyl nitriteHCID 14798Sodium HydroxideHCID 6454002Benz(a)anthracene-7,12-dione, 3-hydroxy-

Product 1

HCID 178526323HCID 178526323, compound

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A solution of sodium hydroxide (0.72 g) in water (0.72 g) is added under stirring at ambient temperature to a suspension of 3-hydroxy-benzo[a]anthracene-7,12-dione, prepared as described in Journal Organic Chemistry (1986) 51 page 3502, (5 g; 18 mmoles) in butanol (25 ml). N-butylnitrite (2 g; 19.4 mmoles) is added over a period of 1 hour to the mixture, which is maintained at 60° C. The reaction mixture is maintained at 60° C. for 4 hours, cooled to ambient temperature and filtered. The solid is washed with toluene (2×10 ml), dried under vacuum and suspended in water (25 ml). Acetic acid (2 ml) is added to the suspension over a period of 30 minutes, operating at ambient temperature under stirring.

Workup

  1. customprepared
  2. temperatureThe reaction mixture is maintained at 60° C. for 4 hours
  3. temperaturecooled to ambient temperature
  4. filtrationfiltered
  5. washThe solid is washed with toluene (2×10 ml)
  6. customdried under vacuum
  7. additionAcetic acid (2 ml) is added to the suspension over a period of 30 minutes
  8. customoperating at ambient temperature

Sources & evidence

ORD record
ord-16749fe7b0004625bc24741ae404d479
Source dataset
uspto-grants-1993_02
Patent number
US05186867

Reaction notes

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