Hydrochloric Acid → HCID 86751465, compound

HRID 1490281Notes

Reaction equation

HRID 1490281 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]2[N:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([Cl:20])[C:4]=2[CH:3]=1.Cl.CO>C(Cl)(Cl)Cl.CCOCC>[ClH:20].[F:1][C:2]1[CH:18]=[CH:17][C:16]2[NH+:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([Cl:20])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67598476HCID 67598476, compound

Product 1

HCID 86751465HCID 86751465, compoundYield 178.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2-fluoro-5-methylquindoline from Example 24 (100 mg) in chloroform (50 mL) was treated at room temperature with a 1M solution of HCl in ether until a yellow solution/precipitate formed. Methanol was added to homogenize the mixture and then the solution was concentrated. The resulting solid was recrystallized from hot CHCl3 (50 mL)/EtOH (5 mL), with a minimum amount of ether being added to facilitate the crystallization process. Filtration, followed by washing the product with diethyl ether and drying afforded 101 mg (90.2%) of the title compound as yellow crystals, mp 211.8°-212.5° C.; 1H NMR (DMSO-d6) δ 13.55 (s, 1H), 8.99 (dd, J=10.0, J=4.4, 1H), 8.82 (d, J=8.4, 1H), 8.40 (dd, J=9.2, J=2.8, 1H), 8.25-8.18 (m, 1H), 7.99 (dt, J=8.4, J=0.8, 1H) , 7.88 (d, J=8.0, 1H), 7.56 (dt, J=8.4, J=0.8, 1H), 5.04 (s, 3H); 13C NMR (DMSO-d6) 160.48 (d, J=250.5), 146.01, 138.95, 134.75, 132.85, 132.53, 127.58 (d, J=5.6), 126.71, 124.94 (d, J=10.6), 122.51 (d, J=9.3), 122.33 (d, J=27.5), 122.20, 114.42, 113.56, 108.44 (d, J=25.4), 40.02; MS (EI, m/z) 285 (M+), 287 (M+2+).

Workup

  1. customformed
  2. concentrationthe solution was concentrated
  3. customThe resulting solid was recrystallized from hot CHCl3 (50 mL)/EtOH (5 mL), with a minimum amount of ether being
  4. additionadded
  5. filtrationFiltration
  6. washby washing the product with diethyl ether
  7. customdrying

Sources & evidence

ORD record
ord-f95baf1b23f24e158553f221b921a536
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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