Sodium Hydroxide → 2,7-Diaminoacridin-9(10H)-one

HRID 1373058Notes

Reaction equation

HRID 1373058 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]2[NH:12][C:11]3[C:6](=[CH:7][C:8]([N+:16]([O-])=O)=[CH:9][CH:10]=3)[C:5](=[O:19])[C:4]=2[CH:3]=1.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[OH-].[Na+].C(=O)(O)[O-].[Na+]>C(O)C.O>[NH2:16][C:8]1[CH:9]=[CH:10][C:11]2[NH:12][C:13]3[C:4](=[CH:3][C:2]([NH2:1])=[CH:15][CH:14]=3)[C:5](=[O:19])[C:6]=2[CH:7]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 73972Sodium sulfide nonahydrateHCID 516892Sodium BicarbonateHCID 210740802-Amino-7-nitroacridin-9(10H)-one

Product 1

HCID 210740792,7-Diaminoacridin-9(10H)-oneYield 94.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

See Bogert et al., 1930. To a stirred suspension of 2-amino-7-nitro-9(10H)-acridone 11 (22.5 g, 88.2 mmol) in ethanol was added, in one lot, a solution of sodium sulphide nonahydrate (94.5 g, 0.394 mol) and sodium hydroxide (37.5 g, 0.938 mol) in water (1.625 L). The mixture was refluxed with stirring for 16 hr. On cooling, saturated sodium bicarbonate solution (250 mL) was added and the total volume of the mixture reduced to 700 mL on a rotary evaporator. The flask was chilled in ice for 3 hr after which the product was collected on a glass sinter. The product was washed with water (4×200 mL) followed by ice-cold ethanol (2×100 mL), dry ether (2×100 mL) and finally hexane (2×100 mL). The product, 12, was dried over P2O5 under vacuum to yield an olive-green solid (18.70 g, 94%).

Workup

  1. additionwas added, in one lot
  2. temperatureThe mixture was refluxed
  3. temperatureOn cooling
  4. customthe total volume of the mixture reduced to 700 mL on a rotary evaporator
  5. temperatureThe flask was chilled in ice for 3 hr after which the product
  6. customwas collected on a glass sinter
  7. washThe product was washed with water (4×200 mL)
  8. dry with materialThe product, 12, was dried over P2O5 under vacuum

Sources & evidence

ORD record
ord-71cd0fb58c5e4ac2bd483127292332b3
Source dataset
uspto-grants-2007_01
Patent number
US07160896B2

Reaction notes

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