Hydrochloric Acid → HCID 13770482, compound

HRID 236325Notes

Reaction equation

HRID 236325 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[CH:13]=[C:14]([C:16](OCC)=[O:17])[N:15]=[C:5]2[C:4]1=O)[CH3:2].[BH4-].[Li+].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]2[CH:13]=[C:14]([CH2:16][OH:17])[N:15]=[C:5]2[CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4148881Lithium borohydrideHCID 13770481HCID 13770481, compound

Product 1

HCID 13770482HCID 13770482, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3.13 g of ethyl 4,5-dihydro-5-ethyl-4-oxo-imidazo-[1,2-a]-quinoxaline-2-carboxylate, 0.5 g of lithium borohydride and 80 ml of anhydrous tetrahydrofuran was refluxed with stirring for 20 hours and the resulting suspension was poured into dilute hydrochloride acid. The mixture was stirred for 10 minutes to break the boron complex and the pale yellow clear solution was made alkaline with sodium carbonate addition. The mixture was extracted with ethyl acetate and the organic phase was evaporated to dryness to obtain 1.93 g of 4,5-dihydro-5-ethyl-imidazo-[1,2-a]-quinoxaline-2-methanol in the form of a buff crystalline solid which was crystallized from ethanol to obtain shiny white plates melting at 160°-165° C. with decomposition.

Workup

  1. temperaturewas refluxed
  2. stirringThe mixture was stirred for 10 minutes
  3. extractionThe mixture was extracted with ethyl acetate
  4. customthe organic phase was evaporated to dryness

Sources & evidence

ORD record
ord-44b0d5efa55c401cb26843c339432af5
Source dataset
uspto-grants-1987_02
Patent number
US04644002

Reaction notes

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