Benzaldehyde → HCID 20362659, compound

HRID 1679360Notes

Reaction equation

HRID 1679360 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.P(=O)(O)(O)O.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][C:30]([NH2:32])=[O:31])[CH:25]=[CH:26][CH:27]=1.[CH:33](=O)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O.C(O)(=O)C>[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]2[CH:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[NH:32][C:30](=[O:31])[CH2:29][CH2:28][C:24]=2[CH:23]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 1004Phosphoric AcidHCID 14812Phosphorus oxide (P4O10)HCID 12240797Benzenepropanamide, 3-methoxy-

Product 1

HCID 20362659HCID 20362659, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

To a mixture of 73 g. of phosphorus pentoxide and 43.5 ml. of 85% phosphoric acid, rendered homogeneous by heating at 170° C., is added at room temperature a solution of 9.0 g. (0.05 moles) of 3-(3-methoxyphenyl)-propionamide and 5.9 g. (0.055 moles) of benzaldehyde in 104 ml. of glacial acetic acid. Stirring under an atmosphere of nitrogen is maintained for 3 days and then the reaction mixture is poured into 1 liter water; a precipitate appears, which is filtered off, washed neutral with water and dried. After separation by chromatography and recrystallization from ethanol, 1.5 g. (11% of theory) of pure 7-methoxy-1-phenyl-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one is obtained. M.P. 185-186° C.

Workup

  1. additionTo a mixture of 73 g
  2. additionis added at room temperature a solution of 9.0 g
  3. temperatureis maintained for 3 days
  4. filtrationwhich is filtered off
  5. washwashed neutral with water
  6. customdried
  7. customAfter separation
  8. customby chromatography and recrystallization from ethanol, 1.5 g

Sources & evidence

ORD record
ord-227710104b4345deb7855780485f89a5
Source dataset
uspto-grants-1978_03
Patent number
US04080449

Reaction notes

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