Benzaldehyde → HCID 20199901, compound

HRID 1834850Notes

Reaction equation

HRID 1834850 reaction equation
[NH2:1][C:2]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].[CH:17](=O)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.S(=O)(=O)(O)O.[BH4-].[Na+]>C(O)(C)C>[CH2:17]([NH:1][C:2]1[CH:15]=[C:14]([CH3:16])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 1118Sulfuric AcidHCID 786512-Amino-4-methylbenzophenoneHCID 4311764Sodium borohydride

Product 1

HCID 20199901HCID 20199901, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 21.1 g. of 2-amino-4-methylbenzophenone, 58.4 g. of benzaldehyde and 35 ml. of isopropanol is added dropwise 5.5 ml. of 46% sulfuric acid while maintaining at temperature of 20°-25° C. There is then slowly added 2.7 g. of sodium borohydride while maintaining 20°-25° C. Thereafter three additional separate and alternate additions of 5.5 mls. of 46% sulfuric acid and 2.7 g. of sodium borohydride are effected while maintaining 20°-25° C. and controlling the foaming caused by the borohydride additions. After stirring for 6 hours there is added with cooling 58 g. of sodium bisulfite in 200 ml. of water followed by the addition of 100 ml. of toluene and stirring for 1.5 hours. The toluene layer is separated, washed twice with water and distilled to remove toluene and benzaldehyde. The cooled residue is treated with heptane which is flashed off and the residue cooled to obtain crystals of 2-benzylamino-4-methylbenzophenone.

Workup

  1. additionTo a mixture of 21.1 g
  2. customThereafter three additional separate
  3. temperaturewhile maintaining 20°-25° C.
  4. additionis added
  5. temperaturewith cooling 58 g
  6. additionof water followed by the addition of 100 ml
  7. stirringof toluene and stirring for 1.5 hours
  8. customThe toluene layer is separated
  9. washwashed twice with water
  10. distillationdistilled
  11. customto remove toluene and benzaldehyde
  12. additionThe cooled residue is treated with heptane which
  13. temperaturethe residue cooled

Sources & evidence

ORD record
ord-acc89ea09a914168b78f6f73785c47fd
Source dataset
uspto-grants-1978_01
Patent number
US04071557

Reaction notes

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