Water → HCID 12813951, compound

HRID 1076505Notes

Reaction equation

HRID 1076505 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:16]#N)[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.S(=O)(=O)(O)[OH:19].N([O-])=O.[Na+].[OH2:27]>>[Cl:1][C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:16]([OH:19])=[O:27])[C:6]3[C:11]([N:12]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1

Participants

5

Reactant 4

HCID 962Water2×HCID 1118Sulfuric AcidHCID 71036109-Acridinecarbonitrile, 2-chloro-HCID 23668193Sodium Nitrite

Product 1

HCID 12813951HCID 12813951, compound

Conditions

Temperature
100 °C

Procedure

A mixture of 19.8 gm of 2-chloro-9-cyano-acridine and 120 cc of 90% sulfuric acid was heated for 3 hours at 100°C and then cooled to 15°-20°C. A solution of 15 gm of sodium nitrite in 30 cc of water was added to the reaction mixture and the mixture was heated at 100°C for 2 hours. After cooling, the reaction mixture was added to a mixture of ice and water and then filtered. The precipitate was washed with water and extracted with a 10% aqueous sodium carbonate solution. The solution was made acidic by the addition of 6N hydrochloric acid, was filtered and the precipitate was washed with water and dried to obtain 10.6 gm of 2-chloro-9-carboxy-acridine melting at a temperature above 300°C. The product was used as such for the next step.

Workup

  1. temperaturecooled to 15°-20°C
  2. temperaturethe mixture was heated at 100°C for 2 hours
  3. temperatureAfter cooling
  4. filtrationfiltered
  5. washThe precipitate was washed with water
  6. extractionextracted with a 10% aqueous sodium carbonate solution
  7. additionThe solution was made acidic by the addition of 6N hydrochloric acid
  8. filtrationwas filtered
  9. washthe precipitate was washed with water
  10. customdried

Sources & evidence

ORD record
ord-b1a0d3f54928411da1013164afa32d5b
Source dataset
uspto-grants-1976_05
Patent number
US03957757

Reaction notes

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