Sodium Hydroxide → 5,7-dichloro-2,3-dihydro-1H-inden-1-amine

HRID 1481347Notes

Reaction equation

HRID 1481347 reaction equation
CO[N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([Cl:14])=[CH:10][C:11]=2[Cl:13])[CH2:6][CH2:5]1.[OH-].[Na+]>C1COCC1>[Cl:14][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([Cl:13])[CH:10]=1)[CH:4]([NH2:3])[CH2:5][CH2:6]2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131736105HCID 131736105, compound

Product 1

HCID 613828355,7-dichloro-2,3-dihydro-1H-inden-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

A solution of BH3 (0.6 mL, 1M in THF) was added to a solution of 5,7-dichloro-2,3-dihydro-1H-inden-1-one O-methyl oxime (0.31 mmol) in 1 mL THF. The reaction mixture was heated to 60° C. for 3 days. An aq. 1M NaOH solution was added and heating to 60° C. was continued for another 24 h. The solvent was removed under vacuo, the residue was diluted with a sat. aq. NaHCO3 solution and extracted 3 times with EtOAc. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the desired product as colorless oil.

Workup

  1. temperatureheating to 60° C.
  2. customThe solvent was removed under vacuo
  3. additionthe residue was diluted with a sat. aq. NaHCO3 solution
  4. extractionextracted 3 times with EtOAc
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-053961c3bff049919787bd340da63f39
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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