Acetic Acid → 2-Chloro-6-nitroquinazolin-4(1H)-one

HRID 1428870Notes

Reaction equation

HRID 1428870 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[N:13]=[C:12](Cl)[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:5]=1.C(O)(=[O:20])C>>[Cl:3][C:4]1[NH:13][C:12](=[O:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:5]=1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 127033662,4-Dichloro-6-nitroquinazoline

Product 1

HCID 1356751542-Chloro-6-nitroquinazolin-4(1H)-oneYield 90%

Procedure

Aqueous 2M NaOH (22.2 mL, 44.4 mmol) was added to 2,4-dichloro-6-nitro-quinazoline (3.61 g, 14.8 mmol). The mixture was sonicated, stirred at room temperature for 3 h, and filtered, rinsing with water (60 mL). Acetic acid (3.81 mL, 66.6 mmol) was added to the filtrate to yield a precipitate, which was collected and dried in a vacuum oven to yield the titled compound (2.99 g, 90% yield). This compound did not yield MS data. 1H NMR (400 MHz, CDCl3): 9.07 (s, 1H), 8.56 (d, J=8.9 Hz, 1H), 7.78 (d, J=8.8 Hz, 1H).

Workup

  1. customThe mixture was sonicated
  2. filtrationfiltered
  3. washrinsing with water (60 mL)
  4. customto yield a precipitate, which
  5. customwas collected
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-07379cd7bb6b4c1ba4c1b7a8d7eaa64b
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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