1H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro- → 6-chloro-2-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dione

HRID 567003

Reaction equation

HRID 567003 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]([Cl:16])[CH:5]=[CH:6]3)[CH:2]=1)=[O:12].Cl.[NH2:18][OH:19]>N1C=CC=CC=1>[Cl:16][C:4]1[CH:5]=[CH:6][C:7]2[C:14](=[O:13])[N:18]([OH:19])[C:11](=[O:12])[C:9]3[C:8]=2[C:3]=1[CH:2]=[CH:1][CH:10]=3

Participants

4

Reactant 2

HCID 776721H,3H-Naphtho[1,8-cd]pyran-1,3-dione, 6-chloro-HCID 443297Hydroxyamine hydrochloride

Product 1

HCID 32363736-chloro-2-hydroxy-1H-benzo[de]isoquinoline-1,3(2H)-dioneYield 80.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chloro-1,8-naphthalic anhydride (1.4 g, 6.0 mmol) and hydroxylamine hydrochloride (0.8 g, 11.5 mmol) were reacted in pyridine (50 mL) following the procedure of Example 1 to give 1.2 g of the title compound, mp 234-236° C.;

Sources & evidence

ORD record
ord-05034fbe28ce4b1aa611a90d1807ced7
Source dataset
uspto-grants-2001_01
Patent number
US06177423B1

Linked notes

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