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

HRID 17791Notes

Reaction equation

HRID 17791 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-374cd19d7f7d4982aa58db9eb4e6c855
Source dataset
uspto-grants-2010_06
Patent number
US07741312B2

Reaction notes

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