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2-Amino-8-hydroxynaphthalene-6-sulfonic acid → 4-Hydroxy-6-m-nitrobenzamido-2-naphthalenesulfonic acid

HRID 745454
Notes
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Reaction equation

HRID 745454 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([OH:15])(=[O:14])=[O:13])[CH:6]=[C:5]2[OH:16].[OH-].[Na+].O.O.O.C([O-])(=O)C.[Na+].[N+:27]([C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34])([O-:29])=[O:28]>O>[OH:16][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:33](=[O:34])[C:32]3[CH:36]=[CH:37][CH:38]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=3)[CH:3]=2)[CH:8]=[C:7]([S:12]([OH:15])(=[O:13])=[O:14])[CH:6]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 70222-Amino-8-hydroxynaphthalene-6-sulfonic acidHCID 8495Benzoyl chloride, 3-nitro-HCID 14798Sodium HydroxideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 129400894-Hydroxy-6-m-nitrobenzamido-2-naphthalenesulfonic acidYield 75.9%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a suspension of 180 g of 6-amino-4-hydroxy-2-naphthalenesulfonic acid in 4 liters of water was added 75 ml of 10N sodium hydroxide. To the resulting solution was added 181.8 g of sodium acetate trihydrate, followed by 190 g of m-nitrobenzoyl chloride. The mixture was stirred vigorously under argon at room temperature for 8 hours and then filtered. The solid was washed with water, ethanol and then ether and dried at room temperature. The resulting brown solid (299.4 g) was added to a mixture of 1500 ml of water and 1200 ml of 1N sodium hydroxide and stirred under argon for one hour. The mixture was filtered and the filtrate was acidified to pH 3 with concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water, ethanol, then ether and dried in vacuo in hot water and gave 221.7 g of 4-hydroxy-6-m-nitrobenzamido-2-naphthalenesulfonic acid, sodium salt.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water, ethanol
  3. dry with materialether and dried at room temperature
  4. additionThe resulting brown solid (299.4 g) was added to a mixture of 1500 ml of water and 1200 ml of 1N sodium hydroxide
  5. stirringstirred under argon for one hour
  6. filtrationThe mixture was filtered
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with water, ethanol
  9. dry with materialether and dried in vacuo in hot water

Sources & evidence

ORD record
ord-72c920b3cfeb4dabb558b3ebf85891d4
Source dataset
uspto-grants-1986_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04599204

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes