Triethylamine → HCID 21460755, compound

HRID 2396321Notes

Reaction equation

HRID 2396321 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 (500mL), separate the organic phase, wash with water, saturated sodium hydrogencarbonate 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 hydrogencarbonate and saturated sodium chloride
  3. customDry
  4. customevaporate the solvent in vacuo
  5. customRecrystallize

Sources & evidence

ORD record
ord-8a270d0db7dc40118e3e3276fd82ec29
Source dataset
uspto-grants-1996_02
Patent number
US05491153

Reaction notes

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