Glycol monoethyl ether → 10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carbonitrile

HRID 1719463Notes

Reaction equation

HRID 1719463 reaction equation
[C:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7]([N+]([O-])=O)=[CH:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]1=2)#[N:2].C([O:23]CCO)C>Cl.[Fe]>[C:1]([N:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:7](=[O:23])[CH2:6][C:5]2[CH:17]=[CH:18][CH:19]=[CH:20][C:4]1=2)#[N:2]

Participants

5

Reactant 2

HCID 8076Glycol monoethyl etherHCID 2246789110-Nitro-5H-dibenz(b,f)azepine-5-carbonitrile

Product 1

HCID 1589587510,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolvent

Procedure

26.3 g (0.1 mole) of 5-cyano-10-nitro-5H-dibenz[b,f]azepine are suspended in a mixture of 265 ml of ethylene glycol monoethyl ether and 75 ml of concentrated hydrochloric acid. 40 g of iron powder are added in small portions at 40° in the course of 40 minutes and the temperature is maintained at 40° by external cooling. The mixture is stirred for a further 2 hours at room temperature, is then heated to 80°, the precipitated product dissolving again, and is filtered through a heated suction filter, which is subsequently washed with ethylene glycol monoethyl ether. The crystallisation which commences in the filtrate is completed by adding 200 ml of water. After cooling for one hour in an ice-bath, filtration is carried out followed by washing with a mixture of ethylene glycol monoethyl ether and water in a ratio of 1:1. 5-cyano-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine is obtained which is identified, by comparing the IR spectra, with material from Example 27.

Workup

  1. temperaturethe temperature is maintained at 40° by external cooling
  2. temperatureis then heated to 80°
  3. dissolutionthe precipitated product dissolving again
  4. filtrationis filtered through a heated suction
  5. filtrationfilter
  6. washwhich is subsequently washed with ethylene glycol monoethyl ether
  7. customThe crystallisation which
  8. additionby adding 200 ml of water
  9. temperatureAfter cooling for one hour in an ice-bath
  10. filtrationfiltration
  11. washby washing with a mixture of ethylene glycol monoethyl ether and water in a ratio of 1:1

Sources & evidence

ORD record
ord-e5ac232298f24dd6beae5ee00d74cb44
Source dataset
uspto-grants-1985_09
Patent number
US04540514

Reaction notes

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