HCID 54279069, compound → 6,11-Dihydrodibenz[b,e]oxepin-11-acetonitrile

HRID 1834477Notes

Reaction equation

HRID 1834477 reaction equation
[C:1]([CH:3]=[C:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)#[N:2]>O>[C:1]([CH2:3][CH:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH2:8][O:7][C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]1=2)#[N:2]

Participants

3

Reactant 1

HCID 54279069HCID 54279069, compound

Product 1

HCID 111282696,11-Dihydrodibenz[b,e]oxepin-11-acetonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A saturated mercury II chloride solution is prepared in 150 ml. dry ether. After the addition of 12 g. aluminium fillings, one leaves the solution to stand for 3 - 5 minutes and, after shaking up twice, decants. The aluminium amalgamated in this manner is now washed several times with absolute ether and finally covered with 300 ml. ether in a stirring apparatus. Subsequently, one mixes with 12 g. 11-(cyanomethylene)-6,11-dihydro-dibenzo-[b,e]-oxepine (0.051 mol), prepared according to C, and adds 12 ml. water thereto in the course of 5 hours, with vigorous stirring. The reaction mixture is then left to stand overnight. The inorganic components are filtered off with suction, the filtrate evaporated in a vacuum and one obtains 11.5 g. (95.5% of theory) of practically pure reduction product of m.p. 85° - 86°. After recrystallising once from a petroleum fraction of m.p. 100° - 140° C., the melting point increases to 87° - 89°. The UV-spectrum shows the absence of the cross-conjugated double bond.

Workup

  1. waitto stand for 3 - 5 minutes
  2. customdecants
  3. additionadds 12 ml
  4. customin the course of 5 hours
  5. waitThe reaction mixture is then left
  6. filtrationThe inorganic components are filtered off with suction
  7. customthe filtrate evaporated in a vacuum and one
  8. customobtains 11.5 g
  9. customAfter recrystallising once from a petroleum fraction of m.p. 100° - 140° C.
  10. temperaturethe melting point increases to 87° - 89°

Sources & evidence

ORD record
ord-46372e499cb84663876d32f2c1744540
Source dataset
uspto-grants-1978_01
Patent number
US04070373

Reaction notes

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