Benzoyl chloride, 3,4,5-trimethoxy- → HCID 13020776, compound

HRID 1156859Notes

Reaction equation

HRID 1156859 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:11])[C:5](=[CH:9][CH:10]=1)[C:6]([OH:8])=[O:7].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[C:17](Cl)=[O:18]>O1CCCC1.CN(C)C1C=CC=CC=1>[CH3:26][O:25][C:21]1[CH:20]=[C:16]([CH:15]=[C:14]([O:13][CH3:12])[C:22]=1[O:23][CH3:24])[C:17]([NH:11][C:4]1[C:5](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=1)[C:6]([OH:8])=[O:7])=[O:18]

Participants

5

Reactant 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 27249674-Fluoroanthranilic acid

Product 1

HCID 13020776HCID 13020776, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 949N,N-DimethylanilineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a mixture of 20 ml of tetrahydrofuran and 1.6 g of dimethylaniline is dissolved 1.6 g of 4-fluoroanthranilic acid. To this solution is added slowly a solution of 2.3 g of 3,4,5-trimethoxybenzoylchloride in tetrahydrofuran under room temperature and the mixture is strred at room temperature for 5 hours. The reaction mixture is concentrated under a reduced pressure, to the residue is added water and hydrochloric acid is added to make the mixture the weakly acidic. The precipitated crystals are collected by filtration and recrystallized from methanol to obtain 2.1 g of N-(3,4,5-trimethoxybenzoyl)-4-fluoroanthranilic acid as colorless needles.

Workup

  1. concentrationThe reaction mixture is concentrated under a reduced pressure, to the residue
  2. additionis added water and hydrochloric acid
  3. additionis added
  4. filtrationThe precipitated crystals are collected by filtration
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-b0a9551ed34d4ab5908428139ed01111
Source dataset
uspto-grants-1982_06
Patent number
US04337270

Reaction notes

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