Hydrochloric Acid → HCID 15684649, compound

HRID 728147Notes

Reaction equation

HRID 728147 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:17]=[C:16]([C:18](OC)=[O:19])[CH:15]=[CH:14][N:13]3[C:22]=2[CH3:23])=[CH:4][C:3]=1[OH:24].[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>O1CCCC1.O.C(OCC)(=O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:11]=[C:12]3[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[CH:14][N:13]3[C:22]=2[CH3:23])=[CH:4][C:3]=1[OH:24]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 15684651HCID 15684651, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15684649HCID 15684649, compoundYield 65.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent4×HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-7-methoxycarbonyl-3-methylimidazo[1,2-a]pyridine (2.0 g) in tetrahydrofuran (50 ml) was dropwise added to a mixture of lithium aluminum hydride (0.7 g) in tetrahydrofuran (60 ml) at -20°~-10° C. over 30 minutes and the mixture was stirred at the same temperature for 30 minutes. To the reaction mixture was dropwise added a mixture of water (10 ml) and tetrahydrofuran (20 ml), and the mixture of ethyl acetate, tetrahydrofuran and water was added thereto. The mixture was adjusted to pH 8 with 6N-hydrochloric acid and the insoluble material was removed by filtration. The separated organic layer from filtrate was washed with brine and dried over magnesium sulfate. The solvent was evaporated and the residue was triturated with a mixture of diethyl ether and ethyl acetate to give 2-[2-(4-amino-3-hydroxyphenyl)ethyl]-7-hydroxymethyl-3-methylimidazo[1,2-a]pyridine (1.19 g).

Workup

  1. additionTo the reaction mixture was dropwise added
  2. additionwas added
  3. customthe insoluble material was removed by filtration
  4. washThe separated organic layer from filtrate was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was triturated with a mixture of diethyl ether and ethyl acetate

Sources & evidence

ORD record
ord-e1ea8c5430784951a07d43430865c723
Source dataset
uspto-grants-1991_09
Patent number
US05047411

Reaction notes

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