Hydrochloric Acid → N-methyl-3,4-dihydro-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

HRID 36081Notes

Reaction equation

HRID 36081 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:19])([CH3:18])[CH:6]=1)=[O:4].[BH4-].[Na+].O1CCCC1.Cl>CO>[CH3:1][NH:2][C:3]([CH:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:19])([CH3:18])[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 15234733N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

Product 1

HCID 15234752N-methyl-3,4-dihydro-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamideYield 78.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.53 g of N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide, 0.38 g of sodium borohydride, 5 ml of tetrahydrofuran, and 5 ml of methyl alcohol was stirred at room temperature for 20 minutes. 2N Hydrochloric acid was added thereto, followed by extracting with dichloromethane. The extract was dried over magnesium sulfate and recrystallized from ethyl acetate and n-hexane to obtain 0.42 g of N-methyl-3,4-dihydro-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide represented by formula shown below.

Workup

  1. extractionby extracting with dichloromethane
  2. dry with materialThe extract was dried over magnesium sulfate
  3. customrecrystallized from ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-a846b74387b142e69bfa74bab82d55b7
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

Loading…