Nitric Acid → 4-Chloro-3-nitro-1,8-naphthalic anhydride

HRID 566970Notes

Reaction equation

HRID 566970 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH:5]1[CH:14]=[C:13]2[C:15]([O:17][C:18](=[O:19])[C:11]3=[C:12]2[C:7](=[C:8]([Cl:20])[CH:9]=[CH:10]3)[CH:6]=1)=[O:16]>S(=O)(=O)(O)O>[CH:5]1[CH:14]=[C:13]2[C:15]([O:17][C:18]([C:11]3=[CH:10][C:9]([N+:1]([O-:4])=[O:2])=[C:8]([Cl:20])[C:7](=[C:12]23)[CH:6]=1)=[O:19])=[O:16]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 776721H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro-

Product 1

HCID 131909924-Chloro-3-nitro-1,8-naphthalic anhydride

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Mixture of concentrated sulfuric acid (2.7 mL) and concentrated nitric acid (2.0 mL) was added to a solution of 4-chloro-1,8-naphthalic anhydride (3.0 g, 12.8 mmol) in concentrated sulfuric acid (10.5 mL) at 0° C. The mixture was stirred at room temperature for 2 hours and poured into ice water (50 mL). The separated solid was filtered, washed with water, and dried to give 2.1 g of the title compound (Reference: Tet., 1995;51(33):9127-9138).

Workup

  1. filtrationThe separated solid was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-c101334f81dd4067a10fdadf334bfdfb
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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