Ethanol → HCID 70633426, compound

HRID 436898Notes

Reaction equation

HRID 436898 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[CH2:7][CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1.[H-].[Na+].[CH:22](OCC)=[O:23].C(O)C>C(OCC)C.O>[ClH:1].[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[C:6](=[O:17])[C:7](=[CH:22][OH:23])[CH2:8][N:9]=[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 8025Ethyl formateHCID 24758Sodium hydrideHCID 12948277HCID 12948277, compound

Product 1

HCID 70633426HCID 70633426, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

The starting material is prepared as follows: To the solution of 2.6 g of 8-chloro-1-phenyl-3,4-dihydro-2-benzazepin-5-one in 4- ml of diethyl ether, 0.5 g of sodium hydride in 10 ml of diethyl ether are added and the mixture stirred for 1/2 hour. Thereupon 1.2 ml of ethyl formate and 0.1 ml of ethanol are added and the mixture refluxed for 24 hours. It is cooled in an ice bath, 30 ml of water are added, the aqueous layer separated, acidified with 2N hydrochloric acid and the precipitate formed filtered off, to yield the 8-chloro-4-hydroxymethlidene-1-phenyl-3,4-dihydro-2-benzazepin-5-one hydrochloride melting at 185° with decomposition.

Workup

  1. customThe starting material is prepared
  2. temperaturethe mixture refluxed for 24 hours
  3. temperatureIt is cooled in an ice bath
  4. customthe aqueous layer separated
  5. customthe precipitate formed
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-b464fc2b03bd4c14aa10f747040dae24
Source dataset
uspto-grants-1977_06
Patent number
US04028381

Reaction notes

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