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Hydrochloric Acid → Hydrochloric Acid

HRID 394221
Notes
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Reaction equation

HRID 394221 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24](F)=[CH:23][C:22]=3F)[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:29].[ClH:30]>C(Cl)Cl.O1CCOCC1>[Cl:30][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:14]1[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[C:18]2[C:13]=1[CH2:12][CH2:11][C:10](=[O:29])[N:9]2[C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8].[ClH:1]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 226480981-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

Product 2

HCID 313Hydrochloric AcidHCID 226481195-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent
HCID 312751,4-DioxaneSolvent

Procedure

Compound 1 (0.95 g, 1.68 mmol), 1a (0.76 g, 2.19 mmol), Pd(PPh3)4 (0.19 g, 0.17 mmol) and LiCl (0.28 g, 6.72 mmol) in 30 mL of dioxane were purged with nitrogen for 3 times and the solution was heated at 108° C. for 20 h. Solvent was removed by vacuum and the residue was dissolved in EtOAc. The organic layer was washed with aqueous NaHCO3, dried with Na2SO4 and was purified by flash chromatography EtOAc/hexane=1:3 to give compound 2. Step B: Compound 2 (1.00 g, 1.68 mmol) in 10 mL of CH2Cl2 was added solution of HCl in dioxane (6.7 mL as 4M solution) and the resulting solution was stirred at rt for 24 h. Volatiles were removed by vacuum to give compound 6 as HCl salt. Mass spectrum (ESI), 499 (M+1).

Workup

  1. customVolatiles were removed by vacuum

Sources & evidence

ORD record
ord-0978437f869a439b8517e7f77c3d68b8
Source dataset
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06809199B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes