Chloroacetone → 1,2,3,4-Tetrahydro-8-methoxy-9-nitro-3-(2-oxopropyl)-5H-[1]benzo-pyrano[3,4-c]pyridin-5-one

HRID 851206Notes

Reaction equation

HRID 851206 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]2[C:12]3[CH2:17][CH2:16][NH:15][CH2:14][C:13]=3[C:18](=[O:20])[O:19][C:5]=2[CH:4]=1.Cl[CH2:22][C:23](=[O:25])[CH3:24]>>[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-:11])=[O:10])=[CH:7][C:6]2[C:12]3[CH2:17][CH2:16][N:15]([CH2:22][C:23](=[O:25])[CH3:24])[CH2:14][C:13]=3[C:18](=[O:20])[O:19][C:5]=2[CH:4]=1

Participants

3

Reactant 2

HCID 6571ChloroacetoneHCID 131369251,2,3,4-Tetrahydro-8-methoxy-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one

Product 1

HCID 131369391,2,3,4-Tetrahydro-8-methoxy-9-nitro-3-(2-oxopropyl)-5H-[1]benzo-pyrano[3,4-c]pyridin-5-oneYield 85.8%

Procedure

Prepared by the method described for Example 26 from 1,2,3,4-tetrahydro-8-methoxy-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one (5.52 g, 0.02 moles) and 1-chloro-2-propanone (3.5 g, 0.038 moles). Recrystallization from methanol gave the product (5.7 g), mp 222°-225° C.

Workup

  1. customPrepared by the method
  2. customRecrystallization from methanol

Sources & evidence

ORD record
ord-2cf31350f6c64d238cbed128d7da28b1
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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