Nitric Acid → 1-Amino-5-chloro-4-nitronaphthalene

HRID 966887Notes

Reaction equation

HRID 966887 reaction equation
[NH:1]([C:5]1[C:14]2[C:9](=[C:10]([Cl:15])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)C(C)=O.[N+:16]([O-])([OH:18])=[O:17].[OH-].[Na+]>CC(O)=O.CCO>[NH2:1][C:5]1[C:14]2[C:9](=[C:10]([Cl:15])[CH:11]=[CH:12][CH:13]=2)[C:8]([N+:16]([O-:18])=[O:17])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 218748441-Acetamino-5-chloronaphthalene

Product 1

HCID 218753321-Amino-5-chloro-4-nitronaphthaleneYield 32%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

1-Acetamino-5-chloronaphthalene (150 mg, 0.68 mmol, prepared as described in Example 213A) was dissolved in 1 mL AcOH and treated with 82 μL of red fuming HNO3 and subsequently deacylated with 1 mL 40% aqueous NaOH solution in 3 mL EtOH according to the procedure described in Example 209A to yield 49 mg (32%) of compound 214A as a yellow solid.

Sources & evidence

ORD record
ord-1685c93469894a5e9edce385102ec151
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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