4-Nitro-1,8-naphthalic anhydride → 2-Hydroxy-6-nitro-benzo[de]isoquinoline-1,3-dione

HRID 566999Notes

Reaction equation

HRID 566999 reaction equation
[CH:1]1[CH:10]=[C:9]2[C:11]([O:13][C:14](=O)[C:7]3=[C:8]2[C:3](=[C:4]([N+:16]([O-:18])=[O:17])[CH:5]=[CH:6]3)[CH:2]=1)=[O:12].Cl.[NH2:20][OH:21]>N1C=CC=CC=1>[OH:21][N:20]1[C:14](=[O:13])[C:7]2[CH:6]=[CH:5][C:4]([N+:16]([O-:18])=[O:17])=[C:3]3[C:8]=2[C:9](=[CH:10][CH:1]=[CH:2]3)[C:11]1=[O:12]

Participants

4

Reactant 2

HCID 811504-Nitro-1,8-naphthalic anhydrideHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 8198652-Hydroxy-6-nitro-benzo[de]isoquinoline-1,3-dioneYield 72.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Nitro-1,8-naphthalic anhydride (2.61 g, 10.7 mmol) and hydroxylamine hydrochloride (1.5 g, 21.4 mmol) were reacted in pyridine (50 mL) following the procedure of Example 1. The crude product was recrystallized from ethanol to give 2.0 g of the title compound, mp 255-260° C.;

Workup

  1. customThe crude product was recrystallized from ethanol

Sources & evidence

ORD record
ord-00bd1af3804e464ca9716b9613743df7
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Reaction notes

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