Isopropanol → 5-Amino-2-(2-propoxyethoxy)benzenesulfonic acid

HRID 1156570Notes

Reaction equation

HRID 1156570 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][C:9]=1[S:17]([O-:20])(=[O:19])=[O:18])[CH2:2][CH3:3].[Na+].[Cl-].[NH4+].C(O)(C)C>O>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][CH2:6][CH2:5][O:4][CH2:1][CH2:2][CH3:3])=[C:9]([S:17]([OH:20])(=[O:19])=[O:18])[CH:10]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 20534989Sodium 2-(2-Propoxyethoxy)-5-nitrobenzenesulfonate

Product 1

HCID 205349995-Amino-2-(2-propoxyethoxy)benzenesulfonic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
77 °C

Procedure

A mixture of 10 g of sodium 2-(2-propoxyethoxy)-5-nitrobenzenesulfonate, 5 g of reduced iron, 0.2 g of ammonium chloride, 20 ml of isopropyl alcohol and 20 ml of water was stirred at 77° C. for 2 hours. After the reaction was completed, the reaction solution was filtered to remove insoluble products. After addition of 10 ml of concentrated hydrochloric acid (36%), the filtrate was cooled. Precipitated crystals were collected by filtration and dried by air. Yield: 7.1 g.

Workup

  1. filtrationthe reaction solution was filtered
  2. customto remove insoluble products
  3. additionAfter addition of 10 ml of concentrated hydrochloric acid (36%)
  4. temperaturethe filtrate was cooled
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration
  7. customdried by air

Sources & evidence

ORD record
ord-a1b87107b6fd446bbcdf56ed94aa840d
Source dataset
uspto-grants-1982_06
Patent number
US04336322

Reaction notes

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