Triethylamine → HCID 5243946, compound

HRID 2370459Notes

Reaction equation

HRID 2370459 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 chloride

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 tetrahydrofuran in a 25 ml flask, triethylamine (1.2 ml, 12 mmol) is added into the solution to obtain a transparent yellow solution. The flask in placed in an ice-water bath, the mixture is stirred under nitrogen protection, propionyl chloride (0.78 ml, 9 mmol) is added drop wise into the mixture. After drop wise addition, the mixture stands at room temperature and is allowed to react. The resulted reactant is subsequently filtered, the filtrate is evaporated to dryness and the residue is separated in a silica column to obtain 1.3 g 3-propionamido-4-methoxybenzoic acid.

Workup

  1. customto obtain a transparent yellow solution
  2. customThe flask in placed in an ice-water bath
  3. additionis added drop wise into the mixture
  4. additionAfter drop wise addition
  5. customstands at room temperature
  6. customto react
  7. filtrationThe resulted reactant is subsequently filtered
  8. customthe filtrate is evaporated to dryness
  9. customthe residue is separated in a silica column

Sources & evidence

ORD record
ord-ce7eceac6b64402a8c6e8a0d329d753a
Source dataset
uspto-grants-2014_04
Patent number
US08710098B2

Reaction notes

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