Nitric Acid → Naphthalic anhydride, 3-nitro-

HRID 1696480Notes

Reaction equation

HRID 1696480 reaction equation
[CH:1]1[CH:2]=[C:3]2[C:8]3=[C:9]([C:11]([O:13][C:14](=[O:15])[C:7]3=[CH:6][CH:5]=[CH:4]2)=[O:12])[CH:10]=1.[N+:16]([O-])([OH:18])=[O:17]>OS(O)(=O)=O>[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=[O:15])[C:7]3=[C:8]2[C:3](=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[CH:6]3)[CH:2]=1)=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 6693Naphthalic anhydride

Product 1

HCID 18194Naphthalic anhydride, 3-nitro-Yield 77.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

To a solution of 1,8-naphthalic anhydride (25 g, 0.13 mol) in conc. H2SO4 (100 mL) was added dropwise a solution of conc. HNO3 (7.85 g, 0.13 mol) in conc. H2SO4 (25 mL) at 0° C. After the addition was complete, the resulting mixture was allowed to warm to RT, stirred for 90 min and then poured into ice-H2O. The solid was filtered by suction, washed with H2O, and re-crystallized from glacial AcOH to yield 3-nitro-1,8-naphthalic anhydride (24.5 g). 1H NMR (300 MHz, CDCl3): δ 9.11 (s, 1H), 9.06 (s, 1H), 8.58 (d, J=7.5 Hz, 1H), 8.43 (d, J=7.8 Hz, 1H), 7.82 (t, J=7.8 Hz, 1H).

Workup

  1. additionAfter the addition
  2. filtrationThe solid was filtered by suction
  3. washwashed with H2O
  4. customre-crystallized from glacial AcOH

Sources & evidence

ORD record
ord-00d9de66b223440db2148f8f7308940b
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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