8-(4-Methyl-3-nitro-benzoylamino)-naphthalene-1,3,5-trisulfonic acid → HCID 365462, compound

HRID 1828688Notes

Reaction equation

HRID 1828688 reaction equation
[CH3:1][C:2]1[CH:32]=[CH:31][C:5]([C:6]([NH:8][C:9]2[C:18]3[C:17]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:16][C:15]([S:23]([OH:26])(=[O:25])=[O:24])=[CH:14][C:13]=3[C:12]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:11][CH:10]=2)=[O:7])=[CH:4][C:3]=1[N+:33]([O-])=O>CO.[Pd]>[NH2:33][C:3]1[CH:4]=[C:5]([CH:31]=[CH:32][C:2]=1[CH3:1])[C:6]([NH:8][C:9]1[C:18]2[C:17]([S:19]([OH:22])(=[O:21])=[O:20])=[CH:16][C:15]([S:23]([OH:26])(=[O:24])=[O:25])=[CH:14][C:13]=2[C:12]([S:27]([OH:30])(=[O:29])=[O:28])=[CH:11][CH:10]=1)=[O:7]

Participants

4

Reactant 1

HCID 119705608-(4-Methyl-3-nitro-benzoylamino)-naphthalene-1,3,5-trisulfonic acid

Product 1

HCID 365462HCID 365462, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

8-(4-Methyl-3-nitro-benzoylamino)-naphthalene-1,3,5-trisulfonic acid (1 eq) and 10% Pd on carbon (10 mol %) are placed in CH3OH. The solution is degassed and an atmosphere of H2 is generated within the reaction vessel. The reaction is allowed to proceed until the uptake of H2 ceases and TLC indicates the disappearance of starting material (12 hrs). The palladium precipitate is removed by filtration through a bed of celite and the filtrate is evaporated to dryness giving the reduced compound 8-(3-Amino-4-methyl-benzoylamino)-naphthalene-1,3,5-trisulfonic acid.

Workup

  1. customThe solution is degassed
  2. customthe disappearance of starting material (12 hrs)
  3. customThe palladium precipitate is removed by filtration through a bed of celite
  4. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-d8218f755fb94f3698a4a50c9d365f7c
Source dataset
uspto-grants-2006_06
Patent number
US07060685B2

Reaction notes

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