Hydroxyamine hydrochloride → N-(3-aminophenyl)-9-(hydroxyimino)-N'-(3-hydroxyphenyl)-9H-fluorene-2,7-disulfonamide

HRID 2120919Notes

Reaction equation

HRID 2120919 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=5)(=[O:27])=[O:26])=[CH:19][CH:20]=4)[C:15](=O)[C:14]=3[CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl.[NH2:38][OH:39]>N1C=CC=CC=1>[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][S:9]([C:12]2[CH:24]=[CH:23][C:22]3[C:21]4[C:16](=[CH:17][C:18]([S:25]([NH:28][C:29]5[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=5)(=[O:26])=[O:27])=[CH:19][CH:20]=4)[C:15](=[N:38][OH:39])[C:14]=3[CH:13]=2)(=[O:10])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 10436736N-(3-Aminophenyl)-N'-(3-hydroxyphenyl)-9-oxo-9H-fluorene-2,7-disulfonamide

Product 1

HCID 85148913N-(3-aminophenyl)-9-(hydroxyimino)-N'-(3-hydroxyphenyl)-9H-fluorene-2,7-disulfonamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product from Example 7A (134 mg, 0.257 mmol) in pyridine (3 mL) was treated with hydroxylamine hydrochloride (20 mg, 0.283 mmol) and stirred at ambient temperature. After 3 hours, the mixture was partitioned between ethyl acetate and 1N HCl. The separated organic phase was washed with 1N HCl, saturated NaHCO3, brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was dissolved in a minimum amount of ethyl acetate and CH2Cl2 was added to effect precipitation. The solid was collected by filtration and dried under reduced pressure to provide the title compound as a white solid (123 mg, 89% yield). 1H NMR (300 MHz, DMSO-d6) δ 13.43 (bs, 1H), 10.17-10.35 (m, 1H), 9.96-10.13 (m, 1H), 9.46 (d, 1H), 8.76 (d, 1H), 8.02-8.18 (m, 3H), 7.8-7.93 (m, 2H), 6.98 (m, 1H), 6.81 (m, 1H), 6.5-6.6 (m, 2H), 6.32-6.44 (m, 2H), 6.16-6.28 (m, 2H), 5.1 (bs, 2H); MS (ESI) 535 (M−H)−.

Workup

  1. customthe mixture was partitioned between ethyl acetate and 1N HCl
  2. washThe separated organic phase was washed with 1N HCl, saturated NaHCO3, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in a minimum amount of ethyl acetate and CH2Cl2
  7. additionwas added to effect precipitation
  8. filtrationThe solid was collected by filtration
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-69117e8e17744957aec3666ec616d04b
Source dataset
uspto-grants-2004_02
Patent number
US06693136B1

Reaction notes

Loading…