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Water → 3-Hydroxy-4-phenylbenzylamine

HRID 2236462
Notes
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Reaction equation

HRID 2236462 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([O:17]C)[CH:6]=1)=[N+]=[N-].O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[N-]=[N+]=[N-]>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([OH:17])[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 33558AzideHCID 593002734-Azidomethyl-2-methoxy-biphenyl

Product 1

HCID 231438563-Hydroxy-4-phenylbenzylamineYield 100.4%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

4-Azidomethyl-2-methoxy-biphenyl (100 mg, 0.42 mmol) is dissolved in THF (5 mL) and H2O (0.5 mL) and to which PPh3 (100 mg, 0.38 mmol) is added. The mixture is allowed to stir at room temperature overnight. After analysis of TLC suggested the disappearance of the starting azide, the reaction is stopped and THF evaporated. The residue is purified through chromatography to provide the title compound (84 mg, 100%).

Workup

  1. customTHF evaporated
  2. customThe residue is purified through chromatography

Sources & evidence

ORD record
ord-c4ba39ed33d5439ab0a16394336b2f0b
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07713994B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes