Water → 1-(Benzenesulfonyl)-1H-indol-5-amine

HRID 84200

Reaction equation

HRID 84200 reaction equation
COC([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15])[CH:9]=[CH:8]2)=O.O.[Cl-].[NH4+:25]>C(Cl)Cl.[Fe]>[C:17]1([S:14]([N:10]2[C:11]3[C:7](=[CH:6][C:5]([NH2:25])=[CH:13][CH:12]=3)[CH:8]=[CH:9]2)(=[O:16])=[O:15])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 575174331H-Indole-5-carboxylic acid, 1-(phenylsulfonyl)-, methyl ester

Product 1

HCID 154501451-(Benzenesulfonyl)-1H-indol-5-amineYield 82.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 6344DichloromethaneSolvent

Procedure

To the suspension of 2 (1.16 g, 3.84 mmol) in WA (38 mL) and water (9 mL), iron (0.64 g, 11.51 mmol) and ammonium chloride (0.41 g, 7.67 mmol) were added and refluxed overnight. After the reaction was filtrated with celite, the solvent was concentrated under reduced pressure to give a brown residue, which was dissolved in CH2Cl2 and quenched with water, followed by extracted with CH2Cl2 (20 mL×3). The combined organic layer was dried over anhydrous MgSO4 and concentrated under reduced pressure to give a brown residue, which was purified by silica gel chromatography (EtOAc:n-hexane=1:2:1% NH3(aq)) to afford 27 (0.86 g). 1H NMR (500 MHz, CD3OD): δ 3.60 (s, 2H), 6.48 (d, J=3.6 Hz, 1H), 6.69 (dd, J=8.7, 2.1 Hz, 1H), 6.76 (d, J=1.8 Hz, 1H), 7.39-7.42 (m, 2H), 7.44 (d, J=3.5 Hz, 1H), 7.49-7.51 (m, 1H), 7.77 (d, J=8.7 Hz, 1H), 7.82 (d, J=7.9 Hz, 2H).

Workup

  1. additionwere added
  2. temperaturerefluxed overnight
  3. filtrationAfter the reaction was filtrated with celite
  4. concentrationthe solvent was concentrated under reduced pressure
  5. customto give a brown residue, which
  6. customquenched with water
  7. extractionby extracted with CH2Cl2 (20 mL×3)
  8. dry with materialThe combined organic layer was dried over anhydrous MgSO4
  9. concentrationconcentrated under reduced pressure
  10. customto give a brown residue, which
  11. customwas purified by silica gel chromatography (EtOAc:n-hexane=1:2:1% NH3(aq))

Sources & evidence

ORD record
ord-b80ae43d1fab46a897ece91672d172cb
Source dataset
uspto-grants-2014_09
Patent number
US08846748B2

Linked notes

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