Acetic Acid → HCID 13137000, compound

HRID 851228Notes

Reaction equation

HRID 851228 reaction equation
[CH2:1]([NH:3][CH:4]([CH3:25])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[C:12]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[C:13]=3[O:14][C:15](=[O:16])[C:8]=2[CH2:7]1)[CH3:2].[C:26]([O-])(=O)[CH3:27].[Na+].C(O)(=O)C.[BH4-].[Na+]>>[CH2:1]([N:3]([CH2:26][CH3:27])[CH:4]([CH3:25])[CH2:5][N:6]1[CH2:11][CH2:10][C:9]2[C:12]3[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[C:13]=3[O:14][C:15](=[O:16])[C:8]=2[CH2:7]1)[CH3:2]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 13136969HCID 13136969, compound

Product 1

HCID 13137000HCID 13137000, compoundYield 21.2%

Procedure

Prepared by the method described in Example 73 from 3-[2-(ethylamino)propyl]-1,2,3,4-tetrahydro-7,8-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one (10.0 g, 0.029 moles), sodium acetate (4.7 g, 0.058 moles), acetic acid (43.2 g, 0.72 moles), and sodium borohydride (5.9 g, 0.16 moles). Several recrystallizations from ethyl acetate/hexane yielded the product as the free base (2.3 g), mp 99°-100° C.

Workup

  1. customPrepared by the method
  2. customSeveral recrystallizations from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c7a42266990b40398535a4f0a5cb637f
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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