HCID 12533738, compound → HCID 10536971, compound

HRID 434706Notes

Reaction equation

HRID 434706 reaction equation
O[NH:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[CH2:14])[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[CH2:4]1>C(O)(=O)C.[Zn]>[NH2:2][CH:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[CH2:14])[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[CH2:4]1

Participants

4

Reactant 1

HCID 12533738HCID 12533738, compound

Product 1

HCID 10536971HCID 10536971, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred slurry of zinc dust (0.9 g, 0.138 mole) in 100 ml of glacial acetic acid stirred in an oil bath at 65° was added 10-hydroxyamino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (10 g, 42 mmole). The mixture was stirred in the oil bath for 2 hours, cooled, and quenched in 500 ml of water. The mixture was made basic with concentrated ammonia, then extracted with ether. The combined ether layers were washed with water, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was recrystallized from hexane to give 7.8 g, m.p. 84.5°-86.5°.

Workup

  1. temperaturecooled
  2. customquenched in 500 ml of water
  3. extractionextracted with ether
  4. washThe combined ether layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe residue was recrystallized from hexane
  9. customto give 7.8 g, m.p. 84.5°-86.5°

Sources & evidence

ORD record
ord-066f1b2ff0604f3ebf83b6c8a6da7bd1
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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