Salicylaldehyde → HCID 53250564, compound

HRID 2169998

Reaction equation

HRID 2169998 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][C:17]1[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=1.[OH:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH:27]=O>O1CCCC1>[CH3:15][O:16][C:17]1[N:22]=[C:21]([NH:23][CH2:27][C:26]2[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=2[OH:24])[CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 6998Salicylaldehyde2×HCID 5800532-Amino-6-methoxypyridine2×HCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 53250564HCID 53250564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

512 mg (2.41 mmol, 1.5 eq) of sodium triacetoxyborohydride are added to a solution of 200 mg (1.61 mmol, 1 eq) of 6-methoxypyridin-2-ylamine (starting material 1) and 236 mg (2.41 mmol, 1 eq) of 2-hydroxybenzaldehyde (starting material 2) in 20 ml of tetrahydrofuran. The solution is stirred at room temperature for 48 h. It is evaporated and the residue is taken up in 100 ml of dichloromethane and then extracted with a saturated aqueous solution of ammonium chloride. The aqueous phase is extracted twice with dichloromethane. The organic phases are combined and dried over sodium sulphate. The residue is chromatographed on silica gel (5/95 ethyl acetate/heptane). 2-[(6-methoxypyridin-2-ylamino)methyl]phenol is obtained in the form of a white solid. Melting point=103° C.

Workup

  1. customIt is evaporated
  2. extractionextracted with a saturated aqueous solution of ammonium chloride
  3. extractionThe aqueous phase is extracted twice with dichloromethane
  4. dry with materialdried over sodium sulphate
  5. customThe residue is chromatographed on silica gel (5/95 ethyl acetate/heptane)

Sources & evidence

ORD record
ord-eb5da2db59fa4c4ba1211fd2a8aac93e
Source dataset
uspto-grants-2015_06
Patent number
US09050266B2

Linked notes

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