Sodium Hydroxide → 6-Amino-1,3-dihydro-2H-indol-2-one

HRID 1937609Notes

Reaction equation

HRID 1937609 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[N+:8]([C:11]1[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[CH:13][C:12]=1[CH2:20][C:21]([OH:23])=O)([O-])=O.[OH-].[Na+]>C(O)C>[NH2:17][C:15]1[CH:16]=[C:11]2[C:12]([CH2:20][C:21](=[O:23])[NH:8]2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2215132,4-Dinitrophenylacetic acidHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 5905386-Amino-1,3-dihydro-2H-indol-2-oneYield 101.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

Tin chloride dihydrate (225 g) was added to a solution of 2,4-dinitrophenylacetic acid (22.6 g) in ethanol (450 mL). The mixture was heated at 90° C. for 10 hours. The reaction mixture was cooled and basified to pH 11 with 12M sodium hydroxide. The solids were removed by filtration and the filtrate was concentrated. The residue was treated with ethanol (300 mL). The insolubles were filtered and washed with ethanol (5×60 mL). The combined ethanol washes were evaporated and dried under vacuum to give 15 g of 6-amino-2-oxindole as a brown powder.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate was concentrated
  4. additionThe residue was treated with ethanol (300 mL)
  5. filtrationThe insolubles were filtered
  6. washwashed with ethanol (5×60 mL)
  7. customThe combined ethanol washes were evaporated
  8. customdried under vacuum

Sources & evidence

ORD record
ord-81066de454ee4034a050986ef9d2cb79
Source dataset
uspto-grants-2002_05
Patent number
US06395734B1

Reaction notes

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