Ammonium Bicarbonate → HCID 21074071, compound

HRID 1593944Notes

Reaction equation

HRID 1593944 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:19])[C:7]3[C:12]([NH:13][C:14]=2[CH:15]=1)=[CH:11][CH:10]=[C:9]([N+:16]([O-])=O)[CH:8]=3.O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+].[OH-].[Na+].C(=O)(O)[O-].[NH4+]>C(O)C.O>[NH2:16][C:9]1[CH:10]=[CH:11][C:12]2[NH:13][C:14]3[C:5](=[CH:4][CH:3]=[C:2]([NH2:1])[CH:15]=3)[C:6](=[O:19])[C:7]=2[CH:8]=1

Participants

7

Reactant 4

HCID 14013Ammonium BicarbonateHCID 14798Sodium HydroxideHCID 73972Sodium sulfide nonahydrateHCID 21074091HCID 21074091, compound

Product 1

HCID 21074071HCID 21074071, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Finely ground 3-amino-7-nitro-9(10H)-acridone (AR-ACO-7, 22.50 g, 88.1 mmol) was suspended in ethanol (950 mL) and stirred at reflux. A solution of sodium sulfide nonahydrate (94.75 g, 394 mmol) and sodium hydroxide (37.5 g, 938 mmol) in water (1.7 L) was added in one lot and refluxing continued for 20 hr. The mixture was allowed to cool to room temperature and ammonium bicarbonate (50 g) was added in one lot and dissolved. The solution was reduced to about 500 mL on a rotary evaporator and allowed to stand overnight. The flask was chilled with ice-water, the product collected, and washed with ice cold water until the filtrate was a pale yellow-green colour. The crude product was dried then dissolved in boiling 1 M hydrochloric acid (900 mL). Charcoal (1 g) was added and the solution filtered whilst hot through a fluted paper. The filtrate was basified to pH 8 by the addition of 0.88 s.g. ammonia and the precipitate collected and was washed with water (2×20 mL) and dried over P2O5 under vacuum to yield a yellow solid AR-ACO-08 (19.85 g, 61.2%).

Workup

  1. temperatureat reflux
  2. temperaturerefluxing
  3. dissolutiondissolved
  4. customThe solution was reduced to about 500 mL on a rotary evaporator
  5. waitto stand overnight
  6. temperatureThe flask was chilled with ice-water
  7. customthe product collected
  8. washwashed with ice cold water until the filtrate
  9. dry with materialThe crude product was dried
  10. dissolutionthen dissolved
  11. additionCharcoal (1 g) was added
  12. filtrationthe solution filtered whilst hot through a fluted paper
  13. additionThe filtrate was basified to pH 8 by the addition of 0.88 s
  14. customammonia and the precipitate collected
  15. washwas washed with water (2×20 mL)
  16. dry with materialdried over P2O5 under vacuum
  17. customto yield a yellow solid AR-ACO-08 (19.85 g, 61.2%)

Sources & evidence

ORD record
ord-882f8a41d04f454ca4a06b05a2a29edb
Source dataset
uspto-grants-2007_11
Patent number
US07300930B2

Reaction notes

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