Hydrochloric Acid → HCID 19760337, compound

HRID 1586976Notes

Reaction equation

HRID 1586976 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([Cl:12])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:13][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.Cl>CO>[ClH:1].[Cl:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([NH:13][C:14]3[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=3)=[CH:3][CH:4]=[N:5]2)=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 111584-Aminobenzaldehyde

Product 1

HCID 19760337HCID 19760337, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4,7-Dichloroquinoline (50 g, 252 mmol) and 4-aminobenzaldehyde (30.6 g, 252 mmol) are stirred in 300 mL of methanol and treated with 126 mL of 2 N HCl. The mixture is boiled on a hot plate and after ~15 minutes, a thick yellow precipitate forms. The heating is continued at a low setting for 3 hours at which point the mixture is allowed to cool to room temperature. The yellow solid is filtered, washed with cold methanol, then ether and dried in vacuo at 60° C. for three days affording 64.65 g (203 mmol, 80% yield) of product: 1H NMR (Me2SO-d6, 300 MHz) δ11.4 (br s, 1H), 10.06 (s, 1H), 8.95 (d,J=9.2 Hz, 1H), 8.65 (d,J=6.9 Hz, 1H), 8.24 (d,J=2.1 Hz, 1H), 8.09 (d,J=8.5 Hz, 2H), 7.92 (d of d,J=2.0, 9.2 Hz, 1H), 7.76 (d,J=8.5 Hz, 2H), 7.13 (d,J=7.0 Hz, 1H).

Workup

  1. waitThe mixture is boiled on a hot plate and after ~15 minutes
  2. filtrationThe yellow solid is filtered
  3. washwashed with cold methanol
  4. dry with materialether and dried in vacuo at 60° C. for three days

Sources & evidence

ORD record
ord-7763d9132d4b48ec9cc5d3fd2bd080f5
Source dataset
uspto-grants-1993_06
Patent number
US05216165

Reaction notes

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