8,8'-[(5-Nitro-1,3-phenylene) bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid → 8,8'-[(5-Amino-m-phenylene)bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid

HRID 2420043Notes

Reaction equation

HRID 2420043 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:35]([NH:37][C:38]2[CH:39]=[C:40]([S:56]([OH:59])(=[O:58])=[O:57])[CH:41]=[C:42]3[C:47]=2[C:46]([S:48]([OH:51])(=[O:50])=[O:49])=[CH:45][C:44]([S:52]([OH:55])(=[O:54])=[O:53])=[CH:43]3)=[O:36])[CH:7]=[C:8]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([S:31]([OH:34])(=[O:33])=[O:32])[CH:16]=[C:17]3[C:22]=2[C:21]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:20][C:19]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:18]3)=[O:11])[CH:9]=1)([O-])=O>[Pd].O>[NH2:1][C:4]1[CH:5]=[C:6]([C:35]([NH:37][C:38]2[CH:39]=[C:40]([S:56]([OH:59])(=[O:58])=[O:57])[CH:41]=[C:42]3[C:47]=2[C:46]([S:48]([OH:51])(=[O:49])=[O:50])=[CH:45][C:44]([S:52]([OH:55])(=[O:54])=[O:53])=[CH:43]3)=[O:36])[CH:7]=[C:8]([C:10]([NH:12][C:13]2[CH:14]=[C:15]([S:31]([OH:34])(=[O:32])=[O:33])[CH:16]=[C:17]3[C:22]=2[C:21]([S:23]([OH:26])(=[O:24])=[O:25])=[CH:20][C:19]([S:27]([OH:30])(=[O:28])=[O:29])=[CH:18]3)=[O:11])[CH:9]=1

Participants

4

Reactant 1

HCID 233351908,8'-[(5-Nitro-1,3-phenylene) bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid

Product 1

HCID 233351918,8'-[(5-Amino-m-phenylene)bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A mixture of 23.0 g of 8,8'-[(5-nitro-1,3-phenylene) bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid, hexasodium salt, 150 ml of water and 2.3 g of 10% palladium catalyst on carbon is hydrogenated at room temperature for 5 hours at an average pressure of 43 lbs, then is filtered through diatomaceous earth and washed with water. The filtrate is then concentrated to a small volume in vacuo, absolute ethanol is added and the resulting oil is triturated until a solid is formed. This material is filtered and washed with absolute ethanol followed by ether. The product is then oven dried at 120° C to give 8,8'-[(5-amino-1,3-phenylene)bis(carbonylimino)]di-1,3,6-naphthalenetrisulfonic acid, hexasodium salt.

Workup

  1. filtrationis filtered through diatomaceous earth
  2. washwashed with water
  3. concentrationThe filtrate is then concentrated to a small volume in vacuo, absolute ethanol
  4. additionis added
  5. customthe resulting oil is triturated until a solid
  6. customis formed
  7. filtrationThis material is filtered
  8. washwashed with absolute ethanol
  9. customoven dried at 120° C

Sources & evidence

ORD record
ord-59ba126dd8164178acc9e9d19ca6dc11
Source dataset
uspto-grants-1978_08
Patent number
US04108890

Reaction notes

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