Water → HCID 67788653, compound

HRID 1757284Notes

Reaction equation

HRID 1757284 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:12]1[CH:21]=[C:20]2[C:15]([C:16](=[O:24])[CH2:17][C:18]([CH2:22][CH3:23])=[N:19]2)=[CH:14][CH:13]=1)(OCC)=[O:8].O.C(OCC)(=O)C>C1COCC1>[CH2:22]([C:18]1[CH2:17][C:16](=[O:24])[C:15]2[C:20](=[CH:21][C:12]([CH2:7][OH:8])=[CH:13][CH:14]=2)[N:19]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 67788991HCID 67788991, compound

Product 1

HCID 67788653HCID 67788653, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (0.6 g) was added to a solution of 7-carboethoxy-2-ethyl-4-quinolone (2.65 g) in THF (200 ml) and the resulting suspension stirred for 2 hours at ambient temperature. Water (100 ml) was slowly added, followed by ethyl acetate (100 ml). The suspension was filtered and washed with ethyl acetate (100 ml). The phases of the filtrate were separated and the aqueous layer re-extracted with ethyl acetate (100 ml). The combined organic phases were dried (MgSO4) and evaporated to give a solid which on recrystallisation from ethyl acetate gave 2-ethyl-7-hydroxymethyl-4-quinolone as a white powder, m.p. 254°-257° C.

Workup

  1. filtrationThe suspension was filtered
  2. washwashed with ethyl acetate (100 ml)
  3. customThe phases of the filtrate were separated
  4. extractionthe aqueous layer re-extracted with ethyl acetate (100 ml)
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. customevaporated
  7. customto give a solid which
  8. customon recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-f621913af1754df4b3f46e2acc07d6c0
Source dataset
uspto-grants-1995_08
Patent number
US05444071

Reaction notes

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