Acetic Anhydride → 1-Acetamino-5-chloronaphthalene

HRID 966885Notes

Reaction equation

HRID 966885 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([N+:12]([O-])=O)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16](OC(C)=O)=[O:17]>CC(O)=O.[Fe]>[NH:12]([C:7]1[C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[CH:10]=[CH:9][CH:8]=1)[C:16]([CH3:15])=[O:17]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 132457431-Chloro-5-nitronaphthalene

Product 1

HCID 218748441-Acetamino-5-chloronaphthaleneYield 95.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

The above synthesized 1-chloro-5-nitronaphthalene (540 mg, 2.6 mmol) was dissolved in 10 mL AcOH, followed by treatment with 415 mg (7.43 mmol) iron powder and subsequently acylated with Ac2O (0.26 mL, 2.73 mmol) according to the procedure described in Example 209A to give 543 mg (95%) of 1-acetamino-5-chloronaphthalene.

Sources & evidence

ORD record
ord-ac54c29781ea4952970945293ebf3b3a
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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