Carbon Dioxide → 2-(3-Phosphonophenylamino)-naphthalene

HRID 2072330

Reaction equation

HRID 2072330 reaction equation
O[C:2]1[C:11](C(O)=O)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=1.[OH-].[Na+].[NH2:17][C:18]1[CH:19]=[C:20]([P:24](=[O:27])([OH:26])[OH:25])[CH:21]=[CH:22][CH:23]=1.S(=O)(O)[O-].[Na+].C(=O)=O.Cl.S(=O)=O>O>[P:24]([C:20]1[CH:19]=[C:18]([NH:17][C:11]2[CH:2]=[CH:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:10]=2)[CH:23]=[CH:22][CH:21]=1)([OH:27])([OH:26])=[O:25]

Participants

9

Reactant 7

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 71043-Hydroxy-2-naphthoic acidHCID 14798Sodium HydroxideHCID 79477Phosphonic acid, P-(3-aminophenyl)-HCID 23665763Sodium Bisulfite

Product 1

HCID 214080912-(3-Phosphonophenylamino)-naphthalene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Water (20 parts) is set stirring and 2-hydroxy-3-naphthoic acid (9.5 parts) charged. Sodium hydroxide liquor (70° Tw -- 6.8 parts) is then added until an alkaline reaction is obtained on Brilliant Yellow test paper. 3-aminophenylphosphonic acid (8.7 parts) and sodium bisulphite liquor (40% -- 100 parts) are charged and the mixture is stirred and boiled under reflux for 18 hours. Carbon dioxide is evolved during the early part of the boiling period. After cooling to 80° C the suspension is acidified with hydrochloric acid (36% -- 59 parts) until acid reaction is obtained on Congo Red paper. During acidification the temperature is raised steadily to the boiling point and the suspension is boiled under reflux for 1-2 hours until evolution of sulphur dioxide has essentially ceased. During this period samples are spotted on to Congo Red test paper to confirm a positive acid reaction. The suspension is then cooled to room temperature, filtered and the cake washed with water (10 parts). The paste (18.2 parts) is dried an air at 50° C to give 12.9 parts of 2-(3-phosphonophenylamino)-naphthalene.

Workup

  1. customis obtained on Brilliant Yellow test paper
  2. temperatureunder reflux for 18 hours
  3. customis obtained on Congo Red paper
  4. temperatureDuring acidification the temperature is raised steadily to the boiling point
  5. customa positive acid reaction
  6. temperatureThe suspension is then cooled to room temperature
  7. filtrationfiltered
  8. washthe cake washed with water (10 parts)
  9. customThe paste (18.2 parts) is dried an air at 50° C

Sources & evidence

ORD record
ord-6b520224b72143d4bca35cc20a7a03f9
Source dataset
uspto-grants-1977_09
Patent number
US04051175

Linked notes

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