Hydrochloric Acid → HCID 19098337, compound

HRID 1975728Notes

Reaction equation

HRID 1975728 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[CH:5][CH:4]=1.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][CH:12]=1.C([BH3-])#N.[Na+].Cl>C1(C)C=CC=CC=1.CO.C(O)(=O)C.O>[ClH:10].[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:7][C:6]2[CH:8]=[CH:9][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:13][CH:12]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 77264-ChlorobenzaldehydeHCID 7732P-AnisidineHCID 5003444Sodium cyanoborohydride

Product 1

HCID 19098337HCID 19098337, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 4-methoxyaniline (75.0 g; 609 mmol) and 4-chlorobenzaldehyde (86.5 g; 615 mmol) in 1000 mL toluene was heated at reflux overnight with removal of water. The solvent was evaporated under reduced pressure, and the resulting light gray solid was taken up in 1500 mL tetrahydrofuran (THF). A solution of sodium cyanoborohydride (38.3 g; 609 mmol) in 180 mL methanol was added. Upon complete addition the reaction was acidified by the slow addition of acetic acid (36 mL). The reaction was stirred at ambient temperature overnight. The mixture was cooled to 0° C. and excess aqueous 6N HCl was added. The resultant precipitate was collected and washed well with diethyl ether to give N-(4-chlorobenzyl)-4-methoxyaniline hydrochloride salt as an off white solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionUpon complete addition the reaction
  3. temperatureThe mixture was cooled to 0° C.
  4. customThe resultant precipitate was collected
  5. washwashed well with diethyl ether

Sources & evidence

ORD record
ord-39e8a8c0261f444fba833efb047cb788
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

Loading…