Acetic Anhydride → 1-Acetamino-5-chloronaphthalene

HRID 2110411Notes

Reaction equation

HRID 2110411 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-3a46e0d9e41a4cb38c67c23d77183d11
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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