Ammonium Chloride → 3-[1-(4-Amino-benzenesulfonyl)-1H-indol-5-yl]-N-hydroxy-acrylamide

HRID 84183Notes

Reaction equation

HRID 84183 reaction equation
[OH:1][NH:2][C:3](=[O:27])[CH:4]=[CH:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:15]([C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=1)(=[O:17])=[O:16])[CH:10]=[CH:9]2.[Cl-].[NH4+]>C(O)(C)C.O.[Fe]>[NH2:24][C:21]1[CH:20]=[CH:19][C:18]([S:15]([N:11]2[C:12]3[C:8](=[CH:7][C:6]([CH:5]=[CH:4][C:3]([NH:2][OH:1])=[O:27])=[CH:14][CH:13]=3)[CH:9]=[CH:10]2)(=[O:17])=[O:16])=[CH:23][CH:22]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 76035046HCID 76035046, compound

Product 1

HCID 760349923-[1-(4-Amino-benzenesulfonyl)-1H-indol-5-yl]-N-hydroxy-acrylamideYield 64.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

Compound 7 was synthesized via the route shown in Scheme 2 in Example 3. A suspension of Compound 6 (0.10 g, 0.26 mmol), iron powder (0.05 g, 0.77 mmol) and ammonium chloride (0.03 g, 0.52 mmol) in isopropyl alcohol (5 ml) and water (1 ml) was refluxed for 4 h. After the reaction mixture was concentrated under reduced pressure, it was quenched with water and extracted with CH2Cl2. The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure. The reaction mixture was purified by silica gel chromatography (CH2Cl2:CH3OH=10:1:1% NH3(aq)) to afford Compound 7 (0.06 g).

Workup

  1. customCompound 7 was synthesized via the route
  2. temperaturewas refluxed for 4 h
  3. concentrationAfter the reaction mixture was concentrated under reduced pressure, it
  4. customwas quenched with water
  5. extractionextracted with CH2Cl2
  6. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe reaction mixture was purified by silica gel chromatography (CH2Cl2:CH3OH=10:1:1% NH3(aq))

Sources & evidence

ORD record
ord-3ca76dd6c0164c479886ef96ad46763a
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Reaction notes

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