2-Naphthol → 1-(4-Chlorophthalazin-1(2H)-ylidene)naphthalen-2(1H)-one

HRID 1711977Notes

Reaction equation

HRID 1711977 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[N:4][N:3]=1.[CH:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][C:14]=1[OH:23].[Cl-].[Al+3].[Cl-].[Cl-]>ClC(Cl)C>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][C:14]=2[OH:23])=[N:3][N:4]=1

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 784901,4-DichlorophthalazineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 1354422751-(4-Chlorophthalazin-1(2H)-ylidene)naphthalen-2(1H)-oneYield 77%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,4-dichlorophthalazine (9.96 g, 50 mmol) in dichloroethane (180 ml) was added 2-naphthol (7.24 g, 50 mmol) and aluminum chloride (7.38 g, 55 mmol) and the mixture was stirred at 80° C. for 17 hrs. The dark red solution was poured in ice water (600 ml) and the resulting brown suspension was stirred vigorously for 1 hr. The solid was collected by filtration, washed with diethyl ether and dried to give 11.8 g of the title compound as a beige solid. (Yield: 77%)

Workup

  1. stirringthe resulting brown suspension was stirred vigorously for 1 hr
  2. filtrationThe solid was collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-96f74f8131624d898fdd91b59d1504c7
Source dataset
uspto-grants-2010_09
Patent number
US07790882B2

Reaction notes

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