Hydrochloric Acid → HCID 4714992, compound

HRID 2232188Notes

Reaction equation

HRID 2232188 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:5]=1[NH2:6].[CH:12](=O)/[CH:13]=[CH:14]/[CH3:15].[OH-].[Na+]>>[CH3:15][C:14]1[CH:13]=[CH:12][C:7]2[C:5](=[C:4]([O:3][CH3:2])[CH:10]=[CH:9][C:8]=2[CH3:11])[N:6]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 84452-Methoxy-5-MethylanilineHCID 14798Sodium HydroxideHCID 447466Crotonaldehyde

Product 1

HCID 4714992HCID 4714992, compoundYield 65%

Conditions

Temperature
80 °C

Procedure

To a solution of 0.34 l concentrated HCl at 40° C. was added 275 parts 2-methoxy-5-methylaniline and further heated to 80° C. Then 154 parts crotonaldehyde was added dropwise, heated to 100° C. for 1 hour. The reaction was cooled to 30° C. and poured into 2.5 l ice water and neutralized with 50% NaOH. The product was filtered, washed with water, water pressed, washed with hexane and air dried to give 65% yield of 2,5-dimethyl-8-methoxyquinoline.

Workup

  1. temperatureheated to 100° C. for 1 hour
  2. temperatureThe reaction was cooled to 30° C.
  3. filtrationThe product was filtered
  4. washwashed with water, water
  5. washwashed with hexane and air
  6. customdried

Sources & evidence

ORD record
ord-d10f060c52df4a688d912bdb52075c3d
Source dataset
uspto-grants-1988_11
Patent number
US04788121

Reaction notes

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