Sodium Hydroxide → HCID 86735704, compound

HRID 372107Notes

Reaction equation

HRID 372107 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:21]3[CH2:22][C:8]4([CH2:12][N:11]([CH2:13][CH:14]5[CH2:18][CH2:17][CH2:16][CH2:15]5)[CH2:10][CH:9]4[C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=43)[C:7]=2[CH:27]=1)=O.Cl.[NH2:29][OH:30].[OH-].[Na+]>C(O)C.O>[CH:1](=[N:29][OH:30])[C:3]1[CH:4]=[CH:5][C:6]2[CH:21]3[CH2:22][C:8]4([CH2:12][N:11]([CH2:13][CH:14]5[CH2:18][CH2:17][CH2:16][CH2:15]5)[CH2:10][CH:9]4[C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=43)[C:7]=2[CH:27]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 20353237HCID 20353237, compound

Product 1

HCID 86735704HCID 86735704, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 6.6 g (0.02 mole) of 5-formyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole (Example 69) and 2.0 g (0.03 mole) of hydroxylamine hydrochloride in 25 ml of ethanol was added dropwise a solution of 1.6 g (.04 mole) of sodium hydroxide in 5 ml of water. The reaction mixture was stirred for 30 minutes and heated under reflux for 5 minutes. A yellow solid precipitated. The reaction mixture was diluted with water, extracted with methylene chloride, and the extract was dried over potassium carbonate and concentrated. The resulting oil was dissolved in ether and filtered. Evaporation of the ether gave the product, 5-formyl-2-cyclopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole oxime, as an oil which was crystallized by the addition of pet. ether. The oxime was dissolved in ether and the solution was acidified to give 3.8 g of the hydrochloride salt; mp. 200° -205° (with dec. starting at 185°).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 minutes
  3. customA yellow solid precipitated
  4. additionThe reaction mixture was diluted with water
  5. extractionextracted with methylene chloride
  6. dry with materialthe extract was dried over potassium carbonate
  7. concentrationconcentrated
  8. dissolutionThe resulting oil was dissolved in ether
  9. filtrationfiltered
  10. customEvaporation of the ether

Sources & evidence

ORD record
ord-daa518e2ec5f402f95fb91ac06366fdc
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

Loading…