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Acetic Acid → (4-((Pyridin-2-ylamino)methyl)phenyl)methanol

HRID 747369
Notes
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Reaction equation

HRID 747369 reaction equation
O[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[NH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1>[N:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[NH:11][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 104392-AminopyridineHCID 5563304-(Hydroxymethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 22018543(4-((Pyridin-2-ylamino)methyl)phenyl)methanolYield 74%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

Using general procedure B: Reaction of 4-hydroxymethyl-benzaldehyde (1.01 g, 7.42 mmol), 2-aminopyridine (697 mg, 7.42 mmol), acetic acid (0.5 mL) and sodium triacetoxyborohydride (3.2 g, 14.8 mmol) in THF (20 mL) at room temperature under N2 for 40 min., then one hour at 50° C., followed by purification of crude material using chromatography on silica gel (2:2:96 CH3OH—NH3 H2O—CH2Cl2), afforded the title compound (1.17 g, 74%) as white foam.

Workup

  1. customone hour at 50° C., followed by purification of crude material

Sources & evidence

ORD record
ord-590dc442cf444255a79a29793759a727
Source dataset
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07396840B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes