Acetic Acid → Ethyl acetate methanol ammonium hydroxide

HRID 1745917Notes

Reaction equation

HRID 1745917 reaction equation
[CH3:1][O:2]C1C=CC2[N:7](C3C=CC4[C:12](=[C:13]([O:20][CH2:21][CH:22]=O)C=CC=4)N=3)C=NC=2C=1.CC(O)=[O:28].CN.[BH-](OC(C)=O)(OC(C)=O)[O:33]C(C)=O.[Na+]>CO.ClCCCl>[CH3:1][OH:2].[CH3:22][CH2:21][O:20][C:13]([CH3:12])=[O:28].[NH4+:7].[OH-:33]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 22227018HCID 22227018, compound

Product 1

HCID 21901312Ethyl acetate methanol ammonium hydroxide

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 887MethanolSolvent

Procedure

[2-(5-Methoxy-benzoimidazol-1-yl)-quinolin-8-yloxy]-acetaldehyde 135A (214 mg, 064 mMol), 400 μL of AcOH, 1.6 mL of a solution of 2 M methylamine in MeOH and Na(OAc)3BH (204, 0.96 mMol) were added to 3 mL of DCE under an atmosphere of dry N2. The reaction mixture was stirred overnight at ambient temperature after which time it was partitioned between DCM and aqueous 1 N NaOH. The DCM layer was washed 2 more times with aqueous 1 N NaOH, then with brine, dried over Na2SO4, filtered and concentrated under vacuum. The resulting residue was chromatographed on flash silica gel initially eluting with MeOH/EtOAc (4:96), then MeOH/EtOAc/NH4OH (8:91.9:0.1), then MeOH/EtOAc/NH4OH (10:89.9:0.1) and finally MeOH/EtOAc/NH4OH (15:84.9:0.1) to give 28 mg of the title compound 135 as a white solid.

Workup

  1. customwas partitioned between DCM and aqueous 1 N NaOH
  2. washThe DCM layer was washed 2 more times with aqueous 1 N NaOH
  3. dry with materialwith brine, dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe resulting residue was chromatographed on flash silica gel
  7. washinitially eluting with MeOH/EtOAc (4:96)

Sources & evidence

ORD record
ord-be5075899e124d6fa8d9912a9b288df0
Source dataset
uspto-grants-2006_03
Patent number
US07019147B1

Reaction notes

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