Triethylamine → HCID 21460755, compound

HRID 2082481Notes

Reaction equation

HRID 2082481 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([O:14]C)=[O:13].[CH2:16](N(CC)CC)C.[C:23]([O:26][C:27]1[C:28](=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:29](Cl)=[O:30])(=[O:25])[CH3:24].C(OCC)(=O)C>O1CCCC1>[C:23]([O:26][C:27]1[CH:35]=[CH:34][CH:33]=[CH:32][C:28]=1[C:29](=[O:30])[CH2:16][NH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([Cl:11])=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:12]([OH:14])=[O:13])(=[O:25])[CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 796682-Acetoxybenzoyl chlorideHCID 15337900HCID 15337900, compound

Product 1

HCID 21460755HCID 21460755, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 3-amino-2-carbmethoxy-6-chloroindole (1 g, 4.4 mmol) in anhydrous tetrahydrofuran (50 mL). Add triethylamine (4.8 mmol) and acetylsalicoyl chloride (4.8 mmol) and stir for 5 minutes. Dilute into ethyl acetate (500 mL), separate the organic phase, wash with water, saturated sodium hydrogen carbonate and saturated sodium chloride. Dry and evaporate the solvent in vacuo. Recrystallize to give the title compound (1.3 g, 79%); mp 184°-86° C.

Workup

  1. customseparate the organic phase
  2. washwash with water, saturated sodium hydrogen carbonate and saturated sodium chloride
  3. customDry
  4. customevaporate the solvent in vacuo
  5. customRecrystallize

Sources & evidence

ORD record
ord-adf186514dc845ad928241dc9dd809f2
Source dataset
uspto-grants-1993_02
Patent number
US05189054

Reaction notes

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