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Hydrochloric Acid → HCID 23370072, compound

HRID 1901051
Notes
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Reaction equation

HRID 1901051 reaction equation
[BH4-].[Na+].B(F)(F)F.[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15](=O)[C:16]1[CH:21]=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:19]([OH:26])=[C:18]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:17]=1.Cl>O1CCCC1>[NH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][CH2:15][C:16]1[CH:17]=[C:18]([C:27]([CH3:28])([CH3:29])[CH3:30])[C:19]([OH:26])=[C:20]([C:22]([CH3:25])([CH3:24])[CH3:23])[CH:21]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6356Boron trifluorideHCID 4311764Sodium borohydrideHCID 23370116N-(2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzamide

Product 1

HCID 23370072HCID 23370072, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a suspension of sodium borohydride (2.72 g) in tetrahydrofuran (80 ml) was added dropwise under ice-cooling BF3, Et20 (8.86 ml) and the mixture was stirred for 30 minutes. To this mixture was added by portions N-(2-aminophenyl )-3,5-di-t-butyl-4-hydroxybenzamide (3.06 g ) and the mixture was stirred overnight while returning slowly to room temperature. 6N hydrochloric acid war added and the mixture was heated under reflux for 30 minutes, the solvent was distilled off and the residue was placed into water, neutralized with sodium hydrogen carbonate, extracted with ethyl acetate, washed with water and saturated saline and dried over anhydrous MgSO4. The solvent was distilled off and the residue was purified by a silica gel column chromatography (hexane:ethyl acetate=4:1) to give (2-aminophenyl)-3,5-di-t-butyl-4-hydroxybenzylamine (2.00 g, 68%) as crystals.

Workup

  1. additionwas added dropwise under ice-
  2. stirringthe mixture was stirred overnight
  3. customwhile returning slowly to room temperature
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 30 minutes
  6. distillationthe solvent was distilled off
  7. extractionextracted with ethyl acetate
  8. washwashed with water and saturated saline
  9. dry with materialdried over anhydrous MgSO4
  10. distillationThe solvent was distilled off
  11. customthe residue was purified by a silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-5bf23823dd06442684d777b9a9816bfa
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05576335

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes