Hydrochloric Acid → 1-Hydroxy-6-nitro-2-indolinone

HRID 1007371

Reaction equation

HRID 1007371 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:5]=1[CH2:13][C:14]([OH:16])=O)([O-])=[O:2].Cl.O.O.[Sn](Cl)Cl>C(O)C.O>[OH:2][N:1]1[C:4]2[C:5](=[CH:6][CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=2)[CH2:13][C:14]1=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrate2×HCID 2215132,4-Dinitrophenylacetic acid

Product 1

HCID 225695621-Hydroxy-6-nitro-2-indolinone

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2.0 g of 2,4-dinitrophenylacetic acid (prepared according to J: Chem. Soc. 1948, 1717) are dissolved in 40 ml ethanol and 6.0 ml of conc. hydrochloric acid and 4.1 g of tin-(II)-chloride-dihydrate are added in batches at ambient temperature. The mixture is stirred for 12 hours at ambient temperature and for 4 hours at 60° C. After cooling another 2.0 g of tin-(II)-chloride-dihydrate are added and the mixture is stirred for another 12 hours at ambient temperature. The reaction mixture is diluted with water, extracted with methylene chloride and the organic phase is dried over sodium sulphate. After elimination of the solvent the residue is triturated with ether and the precipitate is filtered off.

Workup

  1. additionare added
  2. stirringthe mixture is stirred for another 12 hours at ambient temperature
  3. extractionextracted with methylene chloride
  4. dry with materialthe organic phase is dried over sodium sulphate
  5. customAfter elimination of the solvent the residue is triturated with ether
  6. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-8941d20d92524b6298ec0a406b10806a
Source dataset
uspto-grants-2004_09
Patent number
US06794395B1

Linked notes

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