HCID 86676798, compound → HCID 86676797, compound

HRID 473311Notes

Reaction equation

HRID 473311 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]([CH2:30][CH2:31][O:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-])=O)=[CH:35][CH:34]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[CH:6][CH:5]=1)([O-])=O>C(O)C.O.C(O)(=O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][N:12]([CH2:30][CH2:31][O:32][C:33]2[CH:34]=[CH:35][C:36]([NH2:39])=[CH:37][CH:38]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 86676798HCID 86676798, compound

Product 1

HCID 86676797HCID 86676797, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2-[6-([2-(4-nitrophenyl)ethyl]{2-[(4-nitrophenyl)oxy]ethyl}amino)hexyl]-1H-isoindole-1,3(2H)-dione (0.35 g) was dissolved in a mixture of ethanol (40 ml), water (5 ml) and acetic acid (5 ml) and the resulting solution degassed under reduced pressure. 10% Palladium on carbon (56% paste, 0.27 g) was added and the resulting mixture stirred vigorously under a hydrogen atmosphere (atmospheric pressure) for 12 h. The reaction mixture was filtered through Celite™ and washed with ethanol. The filtrate and washings were evaporated to dryness to give the title compound (0.313 g) which was used without further purification.

Workup

  1. customthe resulting solution degassed under reduced pressure
  2. addition10% Palladium on carbon (56% paste, 0.27 g) was added
  3. filtrationThe reaction mixture was filtered through Celite™
  4. washwashed with ethanol
  5. customThe filtrate and washings were evaporated to dryness

Sources & evidence

ORD record
ord-4c017419f1d94b64acea20054beff5c8
Source dataset
uspto-grants-2014_01
Patent number
US08633319B2

Reaction notes

Loading…