Potassium Hydroxide → HCID 19980739, compound

HRID 2052106Notes

Reaction equation

HRID 2052106 reaction equation
C(OC(=O)[C:5]1[C:6](=[CH:10][C:11]([CH3:15])=[CH:12][C:13]=1Cl)[N:7]([CH3:9])[CH3:8])C.[OH-:17].[K+]>O>[CH3:8][N:7]([CH3:9])[C:6]1[CH:5]=[C:13]([OH:17])[CH:12]=[C:11]([CH3:15])[CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 12290793HCID 12290793, compound

Product 1

HCID 19980739HCID 19980739, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethyl-6-chloro-4,N,N-trimethylanthranilate (2.4 g) and KOH (powdered, 1.5 g) were heated together in a test-tube with a free flame. After the initial reaction (temp 200°-220°) had subsided, the temperature was raised to 240°-260°, whereupon a second vigorous reaction ensued and the mixture became dark. On cooling, the mixture was dissolved in water, extracted with ether to remove tarry byproducts, and acidified (pH 5) with acetic acid. The crude product was extracted into chloroform and after removal of solvent, was purified by sublimation at 0.1 mm. 3-Dimethylamino-5-methylphenol was obtained as a pale yellow solid, mp 67°-68°.

Workup

  1. customAfter the initial reaction (temp 200°-220°)
  2. temperaturethe temperature was raised to 240°-260°
  3. temperatureOn cooling
  4. extractionextracted with ether
  5. customto remove tarry byproducts
  6. extractionThe crude product was extracted into chloroform
  7. customafter removal of solvent
  8. customwas purified by sublimation at 0.1 mm

Sources & evidence

ORD record
ord-9afe78d633384a7ab089e5e487174841
Source dataset
uspto-grants-1980_01
Patent number
US04182877

Reaction notes

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