Nitric Acid → 1,2,3,4-Tetrahydro-8-methoxy-9-nitro-5H-[1]benzopyrano[3,4-c]pyridin-5-one

HRID 851197Notes

Reaction equation

HRID 851197 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:5]=2[CH:4]=1.[N+:18]([O-])([OH:20])=[O:19].[OH-].[NH4+]>S(=O)(=O)(O)O.O>[CH3:1][O:2][C:3]1[C:8]([N+:18]([O-:20])=[O:19])=[CH:7][C:6]2[C:9]3[CH2:14][CH2:13][NH:12][CH2:11][C:10]=3[C:15](=[O:17])[O:16][C:5]=2[CH:4]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 14923Ammonium HydroxideHCID 131369188-Methoxy-1,2,3,4-tetrahydro-chromeno[3,4-c]pyridin-5-one

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

1,2,3,4-Tetrahydro-8-methoxy-5H-[1]benzopyrano[3,4-c]pyridin-5-one (1.0 g) is dissolved in a mixture of concentrated sulfuric acid (3 ml) and water (2 ml). The resulting solution is cooled in an ice bath and concentrated nitric acid (1 ml) is added. The reaction mixture is stirred at room temperature for 20 hours. The reaction mixture is poured over ice and made basic with aqueous ammonium hydroxide solution. The product is filtered off and washed with water. Recrystallization from ethanol gave the product (535 mg), mp 200°-205° C. (dec.).

Workup

  1. temperatureThe resulting solution is cooled in an ice bath
  2. additionThe reaction mixture is poured over ice
  3. filtrationThe product is filtered off
  4. washwashed with water
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-63c19099b336440eb082d1ebd998620b
Source dataset
uspto-grants-1983_05
Patent number
US04382939

Reaction notes

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