Sodium Hydroxide → HCID 54179458, compound

HRID 372560Notes

Reaction equation

HRID 372560 reaction equation
[OH-].[Na+].Cl.[Cl:4][C:5]1[CH:18]=[CH:17][C:8]2[CH2:9][CH2:10][CH:11]([NH:15][CH3:16])[CH2:12][C:13](=[O:14])[C:7]=2[CH:6]=1>O>[Cl:4][C:5]1[CH:18]=[CH:17][C:8]2[CH2:9][CH2:10][CH:11]([NH:15][CH3:16])[CH2:12][CH:13]([OH:14])[C:7]=2[CH:6]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131711106HCID 131711106, compound

Product 1

HCID 54179458HCID 54179458, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

Sodium hydroxide solution was added to suspension of 4.6 g of the product of Step B in 100 ml of water cooled to 10° C and the mixture was extracted with methylene chloride. The extracts were dried and evaporated to dryness and the 4 g of oily residue were dissolved in 40 ml of ethanol and 4 ml of water. 2 g of sodium borohydride were added to the mixture at 20° C and the mixture was stirred for an hour. The mixture was evaporated to dryness and the residue was taken up in methylene chloride. The solution was washed with water, dried and evaporated to dryness. The residue was washed with isopropyl ether to obtain 3.7 g of 3-chloro-5ξ-hydroxy-7-methylamino-6,7,8,9-tetrahydro [5H] benzocycloheptene melting at 90° C.

Workup

  1. extractionthe mixture was extracted with methylene chloride
  2. customThe extracts were dried
  3. customevaporated to dryness
  4. dissolutionthe 4 g of oily residue were dissolved in 40 ml of ethanol
  5. addition2 g of sodium borohydride were added to the mixture at 20° C
  6. customThe mixture was evaporated to dryness
  7. washThe solution was washed with water
  8. customdried
  9. customevaporated to dryness
  10. washThe residue was washed with isopropyl ether

Sources & evidence

ORD record
ord-6088029bf0b246da8b337fcd30ae95d3
Source dataset
uspto-grants-1978_05
Patent number
US04091115

Reaction notes

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