Nitric Acid → 6-Nitroquinazoline

HRID 254990Notes

Reaction equation

HRID 254990 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[N:3][CH:2]=1.S(=O)(=O)(O)O.[OH-].[K+].C([O-])([O-])=O.[K+].[K+].[N+:24]([O-])([OH:26])=[O:25]>>[N+:24]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][N:3]=[CH:4]2)([O-:26])=[O:25]

Participants

6

Reactant 5

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 9210QuinazolineHCID 11430Potassium CarbonateHCID 14797Potassium Hydroxide

Product 1

HCID 6002116-Nitroquinazoline

Procedure

Quinazoline (2 g) was nitrated with 25 mL of mixture of nitric acid 90%, 10 mL) and sulfuric acid (+20% SO3, 15 mL) at 0° C. for 20 minutes, and then at ambient temperature for 1 hour. The mixture was then poured on ice, neutralized with KOH and the pH was adjusted to 8 with K2CO3 (pH 8). Filtration and recrystallization from EtOH yielded the crystalline product 6-nitroquinazoline (1.7 g).

Workup

  1. customat 0° C.
  2. customfor 20 minutes
  3. additionThe mixture was then poured on ice
  4. filtrationFiltration and recrystallization from EtOH

Sources & evidence

ORD record
ord-94dcfe81dcc14521bf2cac6b1897154e
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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