Hydrochloric Acid →

HRID 547523Notes

Reaction equation

HRID 547523 reaction equation
[Cl-:1].[NH2:2][C:3]1[CH:25]=[CH:24][C:6]([NH:7][C:8]([C:10]2[CH:11]=[C:12]([CH:21]=[CH:22][CH:23]=2)[NH:13][C:14]2[CH:19]=[CH:18][N+](C)=CC=2)=[O:9])=[CH:5][CH:4]=1.O.[Cl:27][C:28]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]=[CH:30][CH:29]=1.Cl>CCO.CCOC(C)=O.CO.CCCCO>[Cl-:27].[Cl-:1].[CH3:8][N:7]1[CH:6]=[CH:5][CH2+:18]=[CH:19][CH:14]1[NH:13][C:12]1[CH:11]=[C:10]([CH:23]=[CH:22][CH:21]=1)[C:8]([NH:7][C:6]1[CH:5]=[CH:4][C:3]([NH:2][C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH+:31]=[CH:30][CH:29]=2)=[CH:25][CH:24]=1)=[O:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 691404-ChloroquinolineHCID 67201776HCID 67201776, compound

Product 0

No Product data yet.

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 702EthanolSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Compound C6 (100 mg, 0.28 mmol) was dissolved in EtOH (10 mL) and H2O (5 mL) by heating. 4-Chloroquinoline (60 mg, 0.36 mmol) and 3 drops of c.HCl were added, and the mixture refluxed for 18 h (until TLC with the top phase of 5:4:1 mixture of n-BuOH:H2O:CH3CO2H showed complete consumption of starting amine). The reaction mixture was then diluted with EtOAc, boiled for a few minutes and then allowed to cool to room temperature. The resulting precipitate was filtered and crystallized from MeOH/EtOAc to give Cpd. C (64 mg, 63%); mp (MeOH, EtOAc)>300° C.; 1H NMR [(CD3)2SO] δ14.49 (br, 1 H, N+H), 11.01 (s, 1 H, NH), 11.78 (br, 1 H, NH), 10.64 (s, 1 H, NH), 8.77 (d, J=8.5 Hz, 1 H, ArH), 8.57 (d, J=6.5 Hz, 1 H, ArH), 8.32 (d, J=7.5 Hz, 2H, ArH), 8.06-7.92 (m, 6 H, ArH), 7.53 (t, J=7.7 Hz, 1 H, ArH), 7.70-7.65 (m, 1 H, ArH), 7.48 (d, J=8.8 Hz, 2 H, ArH), 7.29 (d, J=7.5 Hz, 2 H, ArH), 6.79 (d, J=6.8 Hz, 1 H, ArH), 3.98 (s, 3 H, N+CH3).

Workup

  1. temperaturethe mixture refluxed for 18 h (until TLC
  2. customH2O:CH3CO2H showed complete consumption of starting amine)
  3. additionThe reaction mixture was then diluted with EtOAc
  4. waitboiled for a few minutes
  5. filtrationThe resulting precipitate was filtered
  6. customcrystallized from MeOH/EtOAc
  7. customto give Cpd

Sources & evidence

ORD record
ord-173184b402904d87904b602ea207fdf5
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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