Ethanol → HCID 86735559, compound

HRID 1679367Notes

Reaction equation

HRID 1679367 reaction equation
[CH3:1][C@H:2]1[C@@H:8]([CH3:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[CH2:5][NH:4][C:3]1=[O:14].C=O.[OH-].[Na+].[CH2:19]([OH:21])C>C(Cl)(Cl)Cl>[CH3:1][C@H:2]1[C@@H:8]([CH3:9])[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[CH2:5][N:4]([CH2:19][OH:21])[C:3]1=[O:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 86735560HCID 86735560, compound

Product 1

HCID 86735559HCID 86735559, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5.7 g. (0.030 moles) of cis-4,5-dimethyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one, 9 ml. (0.09 moles) of 35% aqueous formaldehyde solution and 0.05 g. of sodium hydroxide in 50 ml. of 92% ethanol is heated for 5 hours at 80° C., while stirring. The reaction mixture is cooled and the solvents are evaporated off in vacuo. The oil obtained is taken up in chloroform, washed several times with water and then dried over anhydrous sodium sulfate. After evaporation of the solvent in vacuo, the residual syrup is purified by recrystallization from diisopropyl ether. 4 g. (61% of theory) of cis-4,5-dimethyl-2-hydroxymethyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one are obtained. M.P. 91°-92° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe solvents are evaporated off in vacuo
  3. customThe oil obtained
  4. washwashed several times with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter evaporation of the solvent in vacuo
  7. customthe residual syrup is purified by recrystallization from diisopropyl ether

Sources & evidence

ORD record
ord-0b6c37427700447d9297eeca72791eff
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

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