Methanol → HCID 19427670, compound

HRID 1078550Notes

Reaction equation

HRID 1078550 reaction equation
[OH-:1].[Na+].C([C:5]1[C:6]2[CH:23]=[CH:22][CH:21]=[N:20][C:7]=2[N:8]([CH:17]2[CH2:19][CH2:18]2)[C:9]2[N:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:10]=2[N:11]=1)#N.[CH3:24]O>>[CH:17]1([N:8]2[C:7]3[N:20]=[CH:21][CH:22]=[CH:23][C:6]=3[C:5]([O:1][CH3:24])=[N:11][C:10]3[C:12]([CH3:16])=[CH:13][CH:14]=[N:15][C:9]2=3)[CH2:19][CH2:18]1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 19427675HCID 19427675, compound

Product 1

HCID 19427670HCID 19427670, compoundYield 65%

Procedure

A solution of 2N sodium hydroxide (6 mL, 1.2 mmol) was added in three portions over two hr to a solution of 6-cyano-11-cyclopropyl-4-methyl-11H-dipyrido[3,2-b:2',3'-e][1,4]diazepine (0.30 g, 1.1 mmol) in methanol (50 mL) at room temperature. The mixture was stirred overnight, and then concentrated in vacuo. The residue was dissolved in ethyl acetate (150 mL) and washed succesively with water and brine. After drying (MgSO4), the solution was concentrated and crystallized from acetonitrile to give 0.20 g (65%) of the title compound. A second recrystallization from methanol provided pure product, m.p. 191°-192° C.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. washwashed succesively with water and brine
  4. dry with materialAfter drying (MgSO4)
  5. concentrationthe solution was concentrated
  6. customcrystallized from acetonitrile

Sources & evidence

ORD record
ord-e8b9756279fc441cb8d400058edda47b
Source dataset
uspto-grants-1996_08
Patent number
US05550117

Reaction notes

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