Hydrochloric Acid → 3-Hydroxy-4-[(2-hydroxynaphthalen-1-yl)diazenyl]naphthalene-1-sulfonic acid

HRID 434021Notes

Reaction equation

[CH:1]1[CH:6]=[C:5]2[C:7]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:8][CH:9]([OH:13])[C:10](=[N+:11]=[N-:12])[C:4]2=[CH:3][CH:2]=1.[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[OH:28].C(=O)(O)[O-].[Na+].Cl>O>[OH:13][C:9]1[CH:8]=[C:7]([S:14]([OH:17])(=[O:15])=[O:16])[C:5]2[C:4]([C:10]=1[N:11]=[N:12][C:18]1[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]=1[OH:28])=[CH:3][CH:2]=[CH:1][CH:6]=2

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirring solution of 1-diazo-2-naphthol-4-sulfonic acid (1.49 g, 5.95 mmol) and 2-naphthol (0.858 g, 5.95 mmol) in water (20 mL), sodium bicarbonate (1.50 g, 17.85 mmol) was added slowly. The resulting solution was heated at 60° C. with stirring overnight. The solution was cooled to room temperature, and was adjusted to pH=1 with 3 N hydrochloride solution. The purple precipitate was isolated by filtration and washed with water to provide the title compound (1.35 g, 58%) MS(ES) m/z 393 [M−H].

Workup

temperatureThe solution was cooled to room temperature
customThe purple precipitate was isolated by filtration
washwashed with water

Sources & evidence

ORD record: ord-798bd6fe021e448fa53628f3382a7ef0
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06670387B1

Reaction notes

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