Acetic Acid → HCID 21484746, compound

HRID 1414698Notes

Reaction equation

HRID 1414698 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6]1.C(O)(=[O:23])C>O>[CH:6]([N:5]1[C:13]2[CH:12]=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:2][CH2:3][CH2:4]1)=[O:23]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 21484721HCID 21484721, compound

Product 1

HCID 21484746HCID 21484746, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a suspension of 2.7 g. of 1-(2'-aminoethyl)-3-phenyl-5-chloro-indole hydrochloride in 30 ml. of acetic acid is added a solution of 2.7 g. of chromic anhydride in 3 ml. of water at 10°-15° C. The reaction mixture is stirred for 16 hours at 20° C. The reaction mixture is poured into 500 ml. of water and neutralized to pH 7-8 with ammonia water and extracted with chloroform. The chloroform layer is washed with water and dried over sodium sulfate. The solvent is removed by distillation to an oily residue, to which is added ethanol and insoluble matter is removed by filtration. The filtrate is evaporated to a solidal residue, to which is added isopropanol. After heating, the mixture is cooled to give a light brown insoluble substance, which is removed by filtration. Water is added to the filtrat, and the mixture is extracted with 300 ml. of ether, and ethereal layer was washed with water, dried and thereafter the ether is removed by distillation to give a light yellow-white powder. It is recrystallized from a solvent mixture of ethanol and hexane to give 1-formyl-5-phenyl-7-chloro-2,3-dihydro-1H-1,4-benzodiazepine having a melting point of 245° C. (decomp.). And, the crystals are colored around 230° C.

Workup

  1. additionTo a suspension of 2.7 g
  2. customat 10°-15° C
  3. additionThe reaction mixture is poured into 500 ml
  4. extractionof water and neutralized to pH 7-8 with ammonia water and extracted with chloroform
  5. washThe chloroform layer is washed with water
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed by distillation to an oily residue, to which
  8. additionis added ethanol and insoluble matter
  9. customis removed by filtration
  10. customThe filtrate is evaporated to a solidal residue, to which
  11. additionis added isopropanol
  12. temperatureAfter heating
  13. temperaturethe mixture is cooled
  14. customto give a light brown insoluble substance, which
  15. customis removed by filtration
  16. additionWater is added to the filtrat
  17. extractionthe mixture is extracted with 300 ml
  18. washof ether, and ethereal layer was washed with water
  19. customdried
  20. customthe ether is removed by distillation
  21. customto give a light yellow-white powder
  22. customIt is recrystallized from a solvent mixture of ethanol and hexane

Sources & evidence

ORD record
ord-4d69141d201a4fe59490112558a2bd63
Source dataset
uspto-grants-1977_01
Patent number
US04002611

Reaction notes

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