Water → HCID 12813957, compound

HRID 1576243Notes

Reaction equation

HRID 1576243 reaction equation
S([O-])([O-])(=O)=O.[Cl:6][C:7]1[CH:20]=[CH:19][C:18]2[C:9](=[C:10]([C:22]([O:24][CH3:25])=[O:23])[C:11]3[C:16]([N+:17]=2[CH3:21])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:8]=1.O.[BH4-].[K+]>CO>[Cl:6][C:7]1[CH:20]=[CH:19][C:18]2[N:17]([CH3:21])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]([C:22]([O:24][CH3:25])=[O:23])[C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 1117Sulfate IonHCID 4192641Potassium borohydrideHCID 12814000HCID 12814000, compound

Product 1

HCID 12813957HCID 12813957, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.4 gm of the metho sulfate of 2-chloro-9-methoxycarbonyl-10-methyl-acridinium were suspended in 50 cc of methanol and 2.5 cc of water and after the addition of 5 gm of potassium borohydride, the temperature maintained at 35- 40°C and the mixture was then stirred for 30 minutes at room temperature. The mixture was added to a mixture of ice and water and then filtered. The precipitate was washed with water and then iced methanol and dried to obtain 3.45 gm of 2-chloro-9-methoxycarbonyl-10-methyl-acridane melting at 166°C. The product occurred as a colorless solid soluble in alcohol and chloroform, slightly soluble in ether and insoluble in water. For analysis, the product was recrystallized from methyl ethylketone.

Workup

  1. temperaturethe temperature maintained at 35- 40°C
  2. filtrationfiltered
  3. washThe precipitate was washed with water
  4. dry with materialiced methanol and dried

Sources & evidence

ORD record
ord-13a813b706eb43bf87eb735e11ace808
Source dataset
uspto-grants-1976_09
Patent number
US03979515

Reaction notes

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