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

HRID 278988Notes

Reaction equation

HRID 278988 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-44708f525f254901ae63a395fb1890ca
Source dataset
uspto-grants-2002_03
Patent number
US06362181B1

Reaction notes

Loading…