4-Amino-5-hydroxy-1,7-naphthalenedisulfonic acid → 5-Hydroxy-4-(5-nitro-o-toluamido)-1,7-naphthalenedisulfonic acid

HRID 904038

Reaction equation

HRID 904038 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([S:13]([OH:16])(=[O:15])=[O:14])=[CH:9][C:10]=2[OH:12])[C:5]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:4][CH:3]=1.O.O.O.[C:24]([O-:27])(=O)[CH3:25].[Na+].C[C:30]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][C:31]=1C(Cl)=O>O>[OH:12][C:10]1[CH:9]=[C:8]([S:13]([OH:16])(=[O:15])=[O:14])[CH:7]=[C:6]2[C:11]=1[C:2]([NH:1][C:24]([C:25]1[C:31]([CH3:30])=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=1)=[O:27])=[CH:3][CH:4]=[C:5]2[S:17]([OH:20])(=[O:19])=[O:18]

Participants

5

Reactant 3

HCID 672244-Amino-5-hydroxy-1,7-naphthalenedisulfonic acidHCID 44365682-Methyl-5-nitrobenzoyl chlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 569961365-Hydroxy-4-(5-nitro-o-toluamido)-1,7-naphthalenedisulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 16 g portion of 4-amino-5-hydroxy-1,7-naphthalenedisulfonic acid in 120 ml of water is adjusted to pH 7.2. A 7.6 g portion of sodium acetate trihydrate and 8.8 g of 2-methyl-5-nitrobenzoyl chloride are added with vigorous stirring. The mixture is stirred overnight at room temperature. The solid is then collected by filtration, washed with water, 80% ethanol, ethanol, ether and dried, giving 13.0 g of 5-hydroxy-4-(5-nitro-o-toluamido)-1,7-naphthalenedisulfonic acid, disodium salt.

Workup

  1. filtrationThe solid is then collected by filtration
  2. washwashed with water, 80% ethanol, ethanol, ether
  3. customdried

Sources & evidence

ORD record
ord-58efff5e7dcc495bbcad3b0c38a1c6d8
Source dataset
uspto-grants-1980_10
Patent number
US04229584

Linked notes

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