Hydrochloric Acid → HCID 57309180, compound

HRID 872027Notes

Reaction equation

HRID 872027 reaction equation
[BH4-].[Li+].[O:3]=[C:4]1[CH2:12][C:11]2[C:6](=[CH:7][C:8]([C:13](OC)=[O:14])=[CH:9][CH:10]=2)[NH:5]1.O.Cl>O1CCCC1>[OH:14][CH2:13][C:8]1[CH:7]=[C:6]2[C:11]([CH2:12][C:4](=[O:3])[NH:5]2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 37343722-Oxindole-6-carboxylic acid methyl esterHCID 4148881Lithium borohydride2×

Product 1

HCID 57309180HCID 57309180, compoundYield 20.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Lithium borohydride (228 mg) was added to a suspension of methyl 2-oxoindolin-6-carboxylate (1.0 g) in tetrahydrofuran (10 ml) under ice-cooling and the mixture was stirred at 50° C. for 3 hours. Lithium borohydride (456 mg) was further added and the reaction mixture was stirred at 50° C. for 15 hours. Water was added to the reaction mixture under ice-cooling and the mixture was acidified with addition of conc. hydrochloric acid. It was extracted with ethyl acetate, dried over sodium sulfate and concentrated in vacuo. The resulted residue was triturated in methanol to give 6-(hydroxymethyl)-1,3-dihydro-2H-indol-2-one (172 mg) as a colorless powder. The mother liquid was purified with a silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1 to ethyl acetate) to give the same (242 mg) as a colorless powder.

Workup

  1. temperaturecooling
  2. stirringthe reaction mixture was stirred at 50° C. for 15 hours
  3. temperaturecooling
  4. extractionIt was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulted residue was triturated in methanol

Sources & evidence

ORD record
ord-b476a3b237e448448a3c23235eef7f16
Source dataset
uspto-grants-2015_03
Patent number
US08975252B2

Reaction notes

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