Acetic Acid → HCID 12909654, compound

HRID 1105594Notes

Reaction equation

HRID 1105594 reaction equation
[CH:1]([NH:3][CH:4]([C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-:14])=[O:13])=O.[ClH:22].C(O)(=O)C>O1CCCC1.B>[ClH:22].[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH:4]([NH:3][CH3:1])[CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[N+:12]([O-:14])=[O:13])=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12909642HCID 12909642, compound

Product 1

HCID 12909654HCID 12909654, compound

Reagents, catalysts & solvents 2

HCID 6331BoraneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a cooled mixture of 31.1 g of N-formyl-α-(4-fluorophenyl)-2-nitrophenethylamine in 500 ml of tetrahydrofuran, 441 ml of 0.98 M borane in tetrahydrofuran is added dropwise. The mixture is allowed to stand over the weekend. The mixture is cooled and 100 ml of 5% hydrochloric acid and 20 ml of glacial acetic acid are added cautiously. The solvent is evaporated in vacuum and the residue treated with 10% sodium hydroxide solution. The free amine is extracted with ether and dried over anhydrous sodium sulfate and filtered. Ethereal hydrogen chloride is added dropwise to the filtrate and the product precipitates as the hydrochloride salt. Recrystallization from ethanol gives crystals, mp 241°-243° C. of α-(4-flurophenyl)-N-methyl-2-nitrophenethylamine hydrochloride.

Workup

  1. additionis added dropwise
  2. temperatureThe mixture is cooled
  3. customThe solvent is evaporated in vacuum
  4. additionthe residue treated with 10% sodium hydroxide solution
  5. extractionThe free amine is extracted with ether
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. additionEthereal hydrogen chloride is added dropwise to the filtrate
  9. customthe product precipitates as the hydrochloride salt
  10. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-e8b69812b76844ffab0812742d894f44
Source dataset
uspto-grants-1982_01
Patent number
US04309424

Reaction notes

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