8-Hydroxy-2-quinolinecarboxaldehyde → HCID 178515865, compound

HRID 1436949Notes

Reaction equation

HRID 1436949 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:15][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:25]=1[N:24]=[C:23]([CH:26]=O)[CH:22]=[CH:21]2.[NH2:28][CH2:29][CH2:30][C:31]1[N:35]=[CH:34][NH:33][CH:32]=1>ClC(Cl)C>[NH:33]1[CH:32]=[C:31]([CH2:30][CH2:29][NH:28][CH2:26][C:23]2[CH:22]=[CH:21][C:20]3[C:25](=[C:16]([OH:15])[CH:17]=[CH:18][CH:19]=3)[N:24]=2)[N:35]=[CH:34]1

Participants

5

Reactant 3

HCID 5993428-Hydroxy-2-quinolinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178419017HCID 178419017, compound

Product 1

HCID 178515865HCID 178515865, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Sodium triacetoxyborohydride (225 mg, 1.061 mmol) was added to a stirred solution of 8-hydroxy-quinoline-2-carboxaldehyde 4 (200 mg, 1.156 mmol) and histamine (128 mg, 1.152 mmol) in dichloroethane (10 mL). The mixture was left to stir at RT for 16 h, neutralized (aqueous NaHCO3), and concentrated. The resulting residue, after column chromatography on silica (ethyl acetate/i-PrOH/2 N NH4OH, 6:2:1), afforded 2-{[2-(1H-imidazol-4-yl)-ethylamino]-methyl}-quinolin-8-ol F1 as a straw-colored solid (190 mg, 61%). The above method was repeated using other amines: 2-(aminomethyl)pyridine gave F2 and 2-(2-methylaminoethyl)pyridine gave F3, data given in Table 2.

Workup

  1. waitThe mixture was left
  2. concentrationneutralized (aqueous NaHCO3), and concentrated

Sources & evidence

ORD record
ord-715ae27356e642a09150a2193e8b45c4
Source dataset
uspto-grants-2009_11
Patent number
US07619091B2

Reaction notes

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