Hydrochloric Acid → HCID 67201016, compound

HRID 547576Notes

Reaction equation

HRID 547576 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=1.Cl>CC(O)C>[ClH:1].[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([NH:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][CH:14]=2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9784-Aminobenzoic AcidHCID 691404-Chloroquinoline

Product 1

HCID 67201016HCID 67201016, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolCatalyst

Procedure

To a suspension of 4-chloroquinoline (0.500 g, 3.06 mmol) and 4-aminobenzoic acid (0.419 g, 3.06 mmol) in 2-propanol (10 mL) 3 drops of concentrated hydrochloric acid were added and mixture was microwave irradiated at 150° C. for 1 hour. After cooling solid was filtered off, washed with 2-propanol and dried in vacuo to give Cpd C as a yellow powder. Purity (HPLC): 100%. 1H NMR (DMSO-d6): 7.05 (d, J=6.9 Hz, 1H), 7.64-7.67 (m, 2H), 7.80-7.85 (m, 1H), 8.02-8.17 (m, 5H), 8.59 (d, J=7.2 Hz, 1H), 8.92 (d, J=8.1 Hz, 1H), 11.26 (s, 1H). MS (ES+): calc. for C16H13N2O2 (MH+) 265.1, found 265.1.

Workup

  1. additionwere added
  2. custommixture was microwave irradiated at 150° C. for 1 hour
  3. temperatureAfter cooling solid
  4. filtrationwas filtered off
  5. washwashed with 2-propanol
  6. customdried in vacuo
  7. customto give Cpd C as a yellow powder

Sources & evidence

ORD record
ord-1c23d9e8ebbc463f9b4bb319bf4eff45
Source dataset
uspto-grants-2011_05
Patent number
US07939546B2

Reaction notes

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