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

HRID 24345

Reaction equation

HRID 24345 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 adjusted 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). Insoluble materials were removed by filtration and washed with ethanol (5×60 ml). The combined ethanol solutions were evaporated and the solid obtained was 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. customInsoluble materials were removed by filtration
  6. washwashed with ethanol (5×60 ml)
  7. customThe combined ethanol solutions were evaporated
  8. customthe solid obtained
  9. customwas dried under vacuum

Sources & evidence

ORD record
ord-495d6f7339d542228f12d5bb89aa27ff
Source dataset
uspto-grants-2005_02
Patent number
US06855730B2

Linked notes

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