Triethylamine → HCID 21460755, compound

HRID 1941401Notes

Reaction equation

HRID 1941401 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-db47bd0642a74dd49901b3c81f32cb20
Source dataset
uspto-grants-1997_12
Patent number
US05703107

Reaction notes

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