2,5-Dichlorobenzoic acid → HCID 21110283, compound

HRID 1766333Notes

Reaction equation

HRID 1766333 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[CH2:18][CH2:17][CH2:16]2.C(N(CC)CC)C>S(Cl)(Cl)=O.C1COCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH:12][C:13]1[CH:22]=[CH:21][C:20]2[C:19](=[O:23])[CH2:18][CH2:17][CH2:16][C:15]=2[CH:14]=1)=[O:6]

Participants

6

Reactant 3

HCID 57842,5-Dichlorobenzoic acidHCID 8471TriethylamineHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Product 1

HCID 21110283HCID 21110283, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24386Thionyl ChlorideSolvent

Procedure

Reaction of 2,5-dichlorobenzoic acid (300 mg, 1.50 mmol) in thionyl chloride (3.5 mL) then with 6-Amino-3,4-dihydro-2H-naphthalen-1-one (80 mg, 0.50 mmol) in presence of triethylamine (90 μL, 0.65 mmol) in THF (6 mL) according to method B gave 2,5-dichloro-N-(5-oxo-5,6,7,8-tetrahydro-naphthalen-2-yl)-benzamide (150 mg, 0.48 mmol, 76% yield) as a grey powder after purification by crystallisation in DCM.

Sources & evidence

ORD record
ord-319405e0594941609120e9198a60c399
Source dataset
uspto-grants-2007_06
Patent number
US07230020B2

Reaction notes

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