2-Amino-5-chlorobenzoic acid → HCID 67284465, compound

HRID 1618617Notes

Reaction equation

[CH3:1][C:2]1([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1=O.[NH2:9][C:10]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:11]=1[C:12](O)=O.O=P(Cl)(Cl)[Cl:22]>>[Cl:19][C:16]1[CH:17]=[CH:18][C:10]2[N:9]=[C:3]3[C:2]([CH3:8])([CH3:1])[CH2:6][CH2:5][C:4]3=[C:12]([Cl:22])[C:11]=2[CH:15]=1

Participants

Reactant 3

HCID 124762-Amino-5-chlorobenzoic acid

HCID 24813Phosphorus oxychloride

HCID 1382862,2-Dimethylcyclopentanone

Product 1

HCID 67284465HCID 67284465, compound

Conditions

Temperature: 100 °C

Procedure

2,2-Dimethylcyclopentanone (1.12 g, 10 mmol) and 2-amino-5-chlorobenzoic acid (1.72 g, 10 mmol) were stirred at rt for 10 minutes followed by the addition of POCl3 (10 mL). The resulting mixture was heated to 100° C. for 5 h and overnight at rt. After this time the reaction mixture was poured into ice water and extracted with EtOAc. The solvent was evaporated in vacuo and flash column chromatography on silica (using a gradient of EtOAc/hexane, 0-100% eluent) gave 7,9-dichloro-3,3-dimethyl-2,3-dihydro-1H-cyclopenta[b]quinoline. Mass Spectrum (ESI) m/e=267 (M+1).

Workup

extractionextracted with EtOAc
customThe solvent was evaporated in vacuo and flash column chromatography on silica (

Sources & evidence

ORD record: ord-eae24606a98442ca971bd907731cda5a
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765940B2

Reaction notes

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