Water → HCID 54254134, compound

HRID 361620Notes

Reaction equation

HRID 361620 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[CH3:11])[NH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14].N1C=CC=CC=1.[C:23](Cl)(=[O:25])[CH3:24].O>C1COCC1>[C:23]([NH:1][C:2]1[C:10]2[C:5](=[C:6]([CH3:12])[CH:7]=[CH:8][C:9]=2[CH3:11])[NH:4][C:3]=1[C:13]([O:15][CH3:16])=[O:14])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 53903724HCID 53903724, compound

Product 1

HCID 54254134HCID 54254134, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 0.6 g (2.75 mmol) of methyl 3-amino-4,7-dimethylindole-2-carboxylate, 0.22 ml (3.3 mmol) of pyridine and 15 ml of anhydrous THF was cooled to 0° C. 10 ml of a solution of 0.24 ml (3.3 mmol) of acetyl chloride in anhydrous THF was added dropwise over a period of 30 minutes. After completion of the addition, the reaction mixture was stirred for 30 minutes. The reaction mixture was poured into 200 ml of water and extracted with 30 ml of ethyl acetate three times. The ethyl acetate layers were combined, washed with 100 ml of water once, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to provide 200 mg of white crystals. Yield: 28%

Workup

  1. additionAfter completion of the addition
  2. extractionextracted with 30 ml of ethyl acetate three times
  3. washwashed with 100 ml of water once
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-be2abc9ce3244035ad584e2064f74bb3
Source dataset
uspto-grants-1999_02
Patent number
US05866594

Reaction notes

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