Acetic Acid → 9-Chloro-3-[2-(diethylamino)propyl]-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 851223Notes

Reaction equation

HRID 851223 reaction equation
[Cl:1][C:2]1[C:3]([CH3:23])=[CH:4][C:5]2[O:21][C:20](=[O:22])[C:9]3[CH2:10][N:11]([CH2:14][CH:15]([NH:17][CH2:18][CH3:19])[CH3:16])[CH2:12][CH2:13][C:8]=3[C:6]=2[CH:7]=1.[BH4-].[Na+].[C:26](O)(=O)[CH3:27]>>[Cl:1][C:2]1[C:3]([CH3:23])=[CH:4][C:5]2[O:21][C:20](=[O:22])[C:9]3[CH2:10][N:11]([CH2:14][CH:15]([N:17]([CH2:26][CH3:27])[CH2:18][CH3:19])[CH3:16])[CH2:12][CH2:13][C:8]=3[C:6]=2[CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 131369719-Chloro-3-[2-(ethylamino)propyl]-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Product 1

HCID 131369889-Chloro-3-[2-(diethylamino)propyl]-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Procedure

Prepared by the method described for Example 59 from 9-chloro-3-[2-(ethylamino)propyl]-1,2,3,4-tetrahydro-8-methyl-5H-[1]benzopyrano[3,4-c]pyridin-5-one (0.9 g, 0.003 moles), glacial acetic acid (5 ml), and sodium borohydride (0.6 g, 0.016 moles). Recrystallization from isopropyl ether gave the product (0.45 g), mp 78°-80° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from isopropyl ether

Sources & evidence

ORD record
ord-29f55a7d0a7546d78211f0ad57ea674b
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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