Bicarbonate Ion → Anthraquinone

HRID 1460128

Reaction equation

HRID 1460128 reaction equation
NC1C=C(P(O)(=O)O)C=CC=1.[OH-].[Na+].C(=O)(O)[O-].N[C:19]1[C:32]2[C:31](=[O:33])[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:24](=[O:34])[C:23]=2[C:22](Br)=[CH:21][CH:20]=1>[Cu](Cl)Cl.O>[CH:26]1[C:25]2[C:24](=[O:34])[C:23]3[C:32](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:31](=[O:33])[C:30]=2[CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 769Bicarbonate IonHCID 14798Sodium HydroxideHCID 79477Phosphonic acid, P-(3-aminophenyl)-HCID 6273261-Amino-4-bromoanthraquinone

Product 1

HCID 6780AnthraquinoneYield 240.1%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 962WaterSolvent

Procedure

First of all, 17.3 g (0.1 mol) of 3-aminobenzenephosphonic acid was dispersed in a solution of 70 ml of water and 8 g of sodium hydroxide and mixed throughout. To the mixture, 8 g of sodim bicarbonate and 16 g (0.04 mol) of 1-amino-4-bromoanthraquinone were added and 0.6 g of copper chloride was then added and mixed at 70° to 75° C. until the reaction was terminated. The resultant mixture was filtered and the filtrate was made acidic to remove excess 3-aminobenzenephophonic acid. Sodium chloride was added to the filtrate and salted out, filtered and dried. It was then purified with alcohol to obtain a blue anthraquinone compound (20 g).

Workup

  1. additionmixed throughout
  2. additionmixed at 70° to 75° C. until the reaction
  3. customwas terminated
  4. filtrationThe resultant mixture was filtered
  5. customto remove excess 3-aminobenzenephophonic acid
  6. additionSodium chloride was added to the filtrate
  7. filtrationfiltered
  8. customdried
  9. customIt was then purified with alcohol

Sources & evidence

ORD record
ord-1f06034151e64c81ad06986f5fa0d7dd
Source dataset
uspto-grants-1991_12
Patent number
US05069719

Linked notes

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