Aluminium lithium hydride → 8-(2,6-Diethylbenzylamino)-2,6-dimethyl-3-hydroxymethyl imidazo[1,2-a]pyridine

HRID 1386069Notes

Reaction equation

HRID 1386069 reaction equation
[C:1]([C:6]1[N:10]2[CH:11]=[C:12]([CH3:27])[CH:13]=[C:14]([NH:15][CH2:16][C:17]3[C:22]([CH2:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=3[CH2:25][CH3:26])[C:9]2=[N:8][C:7]=1[CH3:28])(OCC)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:23]([C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:25][CH3:26])[C:17]=1[CH2:16][NH:15][C:14]1[C:9]2[N:10]([C:6]([CH2:1][OH:2])=[C:7]([CH3:28])[N:8]=2)[CH:11]=[C:12]([CH3:27])[CH:13]=1)[CH3:24]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 217173543-Carboethoxy-2,6-dimethyl-8-(2,6-diethylbenzylamino)imidazo[1,2-a]pyridine

Product 1

HCID 217173358-(2,6-Diethylbenzylamino)-2,6-dimethyl-3-hydroxymethyl imidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-carboethoxy-2,6-dimethyl-8-(2,6-diethylbenzylamino)imidazo[1,2-a]pyridine (1.75 g, 4.6 mmol) in 30 ml tetrahydrofuran was treated with lithium aluminiumhydride (0.7 g, 18.5 mmol) at room temperature during 3.5 h. The reaction was complete after 4 h and was quenched carefully by dropwise addition of water (0.7 ml), aqueous sodium hydroxide (0.7 ml, 15%) and again water (2 ml). The mixture was extracted with chloroform and the organic layer was concentrated. The residue was recrystallized in ethanol and the white crystalline product was filtrated, washed with diethyl ether and dried in vacuo, which gave 1.5 g (96%) yield.

Workup

  1. customwas quenched carefully by dropwise addition of water (0.7 ml), aqueous sodium hydroxide (0.7 ml, 15%) and again water (2 ml)
  2. extractionThe mixture was extracted with chloroform
  3. concentrationthe organic layer was concentrated
  4. customThe residue was recrystallized in ethanol
  5. filtrationthe white crystalline product was filtrated
  6. washwashed with diethyl ether
  7. customdried in vacuo, which
  8. customgave 1.5 g (96%)
  9. customyield

Sources & evidence

ORD record
ord-9f138fa14c9e41cab3c9dbbb4360a70c
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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