4-Amino-1-naphthalenesulfonic acid → 4-Benzoylamino-naphthalene-1-sulfonic acid

HRID 2054832

Reaction equation

HRID 2054832 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:4][CH:3]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1>[C:16]([NH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([OH:15])(=[O:13])=[O:14])=[CH:4][CH:3]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 67904-Amino-1-naphthalenesulfonic acidHCID 7412Benzoyl chloride

Product 1

HCID 35301064-Benzoylamino-naphthalene-1-sulfonic acidYield 61.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 4-amino-naphthalene-1-sulfonic acid (2.3 g, 10.0 mmol) in pyridine (15 mL), was added benzoyl chloride (1.4 mL, 12.0 mmol) and the resultant solution was heated at 100° C. and stirred overnight. The solvent was removed in vacuo and the crude material was recrystallized from MeOH (2x) to give the pyridinium salt of 4-benzoylamino-naphthalene-1-sulfonic acid (2.0 g) as a gray colored solid. 1H NMR (300 MHz, DMSO) δ 8.92 (m, 3H), 8.60 (t, 1H), 8.00 (m, 6H), 7.55 (m, 6H); LC/MS m/z 327 (M−H)−.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe crude material was recrystallized from MeOH (2x)

Sources & evidence

ORD record
ord-f875404c6c274782b6694ec0ac3a6e98
Source dataset
uspto-grants-2008_02
Patent number
US07329755B2

Linked notes

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