Methyl Anthranilate → HCID 21442848, compound

HRID 1606512Notes

Reaction equation

HRID 1606512 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[Cl:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25]CO)[CH2:21][CH2:20]2)[CH:16]=[CH:17][CH:18]=1.[Na]>C1(C)C=CC=CC=1>[C:1]([O:10][CH2:11][CH2:25][N:22]1[CH2:21][CH2:20][N:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([Cl:12])[CH:14]=2)[CH2:24][CH2:23]1)(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4]

Participants

5

Reactant 3

HCID 8635Methyl AnthranilateHCID 967031-Piperazineethanol, 4-(3-chlorophenyl)-HCID 5360545Sodium

Product 1

HCID 21442848HCID 21442848, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10.6 G. (0.07 mol) of methyl anthranilate, 12.1 g. (0.05 mol) of 2-(4-m-chlorophenylpiperazino)-ethanol, 150 ml. of dry toluene and 0.09 g. of sodium are heated in a distillation apparatus for 2 1/2 hours on an oil bath, while slowly distilling the methanol eliminated in the transesterification reaction. The toluene solution is filtered while hot to remove a small amount of insoluble matter, the toluene is evaporated from the filtrate, and the residue is triturated in petroleum ether, filtered and recrystallised from isopropyl alcohol to give 13 g. (yield = 72%) of 2-(4-m-chlorophenylpiperazino)-ethyl anthranilate, which melts at 77°C., and which is found to be identical to the product prepared in Example 18 using a mixed melting point.

Workup

  1. distillationwhile slowly distilling the methanol
  2. customeliminated in the transesterification reaction
  3. filtrationThe toluene solution is filtered while hot
  4. customto remove a small amount of insoluble matter
  5. customthe toluene is evaporated from the filtrate
  6. customthe residue is triturated in petroleum ether
  7. filtrationfiltered
  8. customrecrystallised from isopropyl alcohol
  9. customto give 13 g

Sources & evidence

ORD record
ord-8f451d9b2478428da3285cfa014289ae
Source dataset
uspto-grants-1976_04
Patent number
US03953449

Reaction notes

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