Hydrochloric Acid → HCID 58386371, compound

HRID 74535Notes

Reaction equation

HRID 74535 reaction equation
[CH:1]1([CH:4]=[C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]2=O)[CH2:3][CH2:2]1.B.CO.Cl>C1COCC1>[CH:1]1([CH2:4][CH:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH2:6]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6331BoraneHCID 673385303-Cyclopropylmethylene-1,3-dihydro-indol-2-one

Product 1

HCID 58386371HCID 58386371, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1.0 g (5.4 mmol) 3-cyclopropylmethylene-1,3-dihydro-indol-2-one were placed in 50 mL THF. 12 mL (12 mmol) 1M borane in THF was slowly added dropwise. The reaction mixture was refluxed for 3 h. After cooling to RT 10 mL methanol and 15 mL semi-concentrated aqueous hydrochloric acid solution were successively added dropwise and then the mixture was refluxed for 3 h. After cooling to RT it was extracted with EtOAc. The aqueous phase was made alkaline with aqueous 4M sodium hydroxide solution and extracted once again with EtOAc. The organic phase was dried, filtered and evaporated down.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. additionwere successively added dropwise
  3. temperaturethe mixture was refluxed for 3 h
  4. extractionwas extracted with EtOAc
  5. extractionextracted once again with EtOAc
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated down

Sources & evidence

ORD record
ord-df417d6fac5d419e8972633d8451b21d
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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