10-hydroxyimino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene → HCID 12533738, compound

HRID 434701Notes

Reaction equation

HRID 434701 reaction equation
[OH:1][N:2]=[C: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([BH3-])#N.[Na+]>CO>[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)[OH:1]

Participants

4

Reactant 2

HCID 82670410-hydroxyimino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 12533738HCID 12533738, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A mixture of 15.3 of oxime from Step D, 500 ml of methanol, 12 g of sodium cyanoborohydride in 450 ml of methanol was treated dropwise with a solution of 12 ml of 12N hydrochloric in 50 ml of methanol over 5 hours, and then stirred overnight at room temperature. The solvent was evaporated, the residue was stirred with 200 ml of 1N aqueous hydrochloric acid, made alkaline with concentrated ammonium hydroxide and extracted with 3×175 ml of ether. The combined extracts were dried (Na2SO4), filtered and evaporated. The crystalline residue was washed with methanol to give 9.6 g of 10-hydroxamino-5-methylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepten, m.p. 145°-147° C.

Workup

  1. customThe solvent was evaporated
  2. stirringthe residue was stirred with 200 ml of 1N aqueous hydrochloric acid
  3. extractionextracted with 3×175 ml of ether
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated
  7. washThe crystalline residue was washed with methanol

Sources & evidence

ORD record
ord-e06f64b8af184aeb8bc1035af66c70ea
Source dataset
uspto-grants-1983_08
Patent number
US04399141

Reaction notes

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