Propionic Acid → HCID 13136999, compound

HRID 851227Notes

Reaction equation

HRID 851227 reaction equation
Cl.Cl.[CH2:3]([NH:5][CH:6]([CH3:27])[CH2:7][N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[CH:19][C:15]=3[O:16][C:17](=[O:18])[C:10]=2[CH2:9]1)[CH3:4].C([O-])(=O)C.[Na+].[BH4-].[Na+].[C:35](O)(=O)[CH2:36][CH3:37]>>[CH2:3]([N:5]([CH2:35][CH2:36][CH3:37])[CH:6]([CH3:27])[CH2:7][N:8]1[CH2:13][CH2:12][C:11]2[C:14]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[CH:19][C:15]=3[O:16][C:17](=[O:18])[C:10]=2[CH2:9]1)[CH3:4]

Participants

5

Reactant 4

HCID 1032Propionic AcidHCID 517045Sodium AcetateHCID 4311764Sodium borohydrideHCID 13136968HCID 13136968, compound

Product 1

HCID 13136999HCID 13136999, compoundYield 38.6%

Procedure

Prepared by the method described in Example 73 from 3-[2-(ethylamino)propyl]-1,2,3,4-tetrahydro-8,9-dimethoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one dihydrochloride (6.7 g, 0.016 moles), sodium acetate (2.6 g, 0.032 moles), sodium borohydride (3.3 g, 0.087 moles), and propionic acid (29.8 g, 0.40 moles) instead of acetic acid. Several recrystallizations from diisopropyl ether yielded the product as the free base (2.4 g), mp 93°-96° C.

Workup

  1. customPrepared by the method
  2. customSeveral recrystallizations from diisopropyl ether

Sources & evidence

ORD record
ord-604b4e46c849481ca99c33740f260fe2
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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