8-[4-(4-Nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid → 8-[4-(4-Amino-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid

HRID 2166509Notes

Reaction equation

HRID 2166509 reaction equation
[N+:1]([C:4]1[CH:47]=[CH:46][C:7]([C:8]([NH:10][C:11]2[CH:41]=[CH:40][C:14]([C:15]([NH:17][C:18]3[CH:19]=[C:20]([S:36]([OH:39])(=[O:38])=[O:37])[CH:21]=[C:22]4[C:27]=3[C:26]([S:28]([OH:31])(=[O:30])=[O:29])=[CH:25][C:24]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:23]4)=[O:16])=[C:13]([S:42]([OH:45])(=[O:44])=[O:43])[CH:12]=2)=[O:9])=[C:6]([S:48]([OH:51])(=[O:50])=[O:49])[CH:5]=1)([O-])=O>[Pd].O>[NH2:1][C:4]1[CH:47]=[CH:46][C:7]([C:8]([NH:10][C:11]2[CH:41]=[CH:40][C:14]([C:15]([NH:17][C:18]3[CH:19]=[C:20]([S:36]([OH:39])(=[O:37])=[O:38])[CH:21]=[C:22]4[C:27]=3[C:26]([S:28]([OH:31])(=[O:29])=[O:30])=[CH:25][C:24]([S:32]([OH:35])(=[O:34])=[O:33])=[CH:23]4)=[O:16])=[C:13]([S:42]([OH:45])(=[O:43])=[O:44])[CH:12]=2)=[O:9])=[C:6]([S:48]([OH:51])(=[O:50])=[O:49])[CH:5]=1

Participants

4

Reactant 1

HCID 131521248-[4-(4-Nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid

Product 1

HCID 131521268-[4-(4-Amino-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A reaction mixture comprising 17.5 g of 8-[4-(4-nitro-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid, pentasodium salt, 1.0 g of 10% palladium on carbon catalyst and 100 ml of water was hydrogenated in a Parr shaker for one hour and then filtered through diatomaceous earth. The filtrate was concentrated to about 65 ml and then poured with vigorous stirring into 500 ml of absolute ethanol. The granular precipitate was collected by filtration, washed with ethanol, then ether and dried for three days at 110° C., giving 8-[4-(4-amino-2-sulfobenzamido)-2-sulfobenzamido]-1,3,6-naphthalenetrisulfonic acid, pentasodium salt.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. concentrationThe filtrate was concentrated to about 65 ml
  3. additionpoured
  4. filtrationThe granular precipitate was collected by filtration
  5. washwashed with ethanol
  6. dry with materialether and dried for three days at 110° C.

Sources & evidence

ORD record
ord-06d4d3a6771d43c0b1255f74ef3e12fb
Source dataset
uspto-grants-1983_06
Patent number
US04387059

Reaction notes

Loading…