Water → Acridine-9-carboxylic acid

HRID 1244768Notes

Reaction equation

HRID 1244768 reaction equation
[C:1]([C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)#N.N([O-])=[O:18].[Na+].[OH2:21]>S(=O)(=O)(O)O.[OH-].[Na+]>[C:1]([C:3]1[C:4]2[C:9]([N:10]=[C:11]3[C:16]=1[CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:8][CH:7]=[CH:6][CH:5]=2)([OH:18])=[O:21]

Participants

6

Reactant 3

HCID 962WaterHCID 947199-AcridinecarbonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 94721Acridine-9-carboxylic acid

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

Part of the product of the above procedure, that is, 9-cyano acridine (4 g) is dissolved in sulphuric acid containing 10% by weight of distilled water (total volume equals 40 cm3). The mixture thus obtained is heated at a temperature of 100° C. for 2 hours after which time sodium nitrite (10.7 g) is added slowly with continuous stirring. The resulting mixture is heated at 100° C. for 2 hours then poured into cold, distilled water (650 cm3) The solid material which precipitates at this stage is isolated by filtration and allowed to dissolve in the minimum quantity of one molar sodium hydroxide solution; the solution thus obtained is filtered and the filtrate made slightly acidic by the addition of a 50%, by volume, solution of sulphuric acid in water. The 9-carboxy-acridine so formed is then dried in vacuo.

Workup

  1. customThe mixture thus obtained
  2. additionis added slowly with continuous stirring
  3. additionthen poured into cold,
  4. distillationdistilled water (650 cm3) The solid material which
  5. customprecipitates at this stage
  6. customis isolated by filtration
  7. customthe solution thus obtained
  8. filtrationis filtered
  9. additionthe filtrate made slightly acidic by the addition of a 50%, by volume, solution of sulphuric acid in water

Sources & evidence

ORD record
ord-302b1984d5194bd0821890e2c69958b4
Source dataset
uspto-grants-2006_10
Patent number
US07122671B1

Reaction notes

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