Triethylamine → HCID 5243946, compound

HRID 2370436Notes

Reaction equation

HRID 2370436 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].C(N(CC)CC)C.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>O1CCCC1>[C:20]([NH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6])(=[O:23])[CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 178233-Amino-4-methoxybenzoic acidHCID 62324Propionyl chloride2×

Product 1

HCID 5243946HCID 5243946, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.6 g 3-amino-4-methoxybenzoic acid (1.0 g, 6 mmol) is dissolved in dry THF (tetrahydrofuran) in a 25 ml flask, triethylamine (1.2 ml, 12 mmol) is subsequently added to obtain transparent yellow solution. The mixture is stirred under nitrogen protection, propionyl chloride (0.78 ml, 9 mmol) is added into the flask in an ice-water bath. After finishing addition of propionyl chloride the mixture is naturally raised to room temperature. The reacted mixture is filtered, the filtrate is evaporated to dryness and separated using a silica column to obtain 3-propionamido-4-methoxybenzoic acid 1.3 g (yield: 67%).

Workup

  1. customto obtain transparent yellow solution
  2. additionis added into the flask in an ice-water bath
  3. filtrationThe reacted mixture is filtered
  4. customthe filtrate is evaporated to dryness
  5. customseparated

Sources & evidence

ORD record
ord-3f736753d1dd402d9263a4a72e27bd66
Source dataset
uspto-grants-2014_04
Patent number
US08710098B2

Reaction notes

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