Hydrochloric Acid → Ethyl 2-benzoyl-6chloro-3-[(methoxycarbonyl)amino]-1H-indole-1-caboxylate

HRID 651007Notes

Reaction equation

HRID 651007 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[Cl:11])[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:3]=1[C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.N1C=CC=CC=1.Cl[C:32]([O:34][CH3:35])=[O:33].Cl>ClCCl>[C:17]([C:3]1[N:4]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2[C:6]([C:2]=1[NH:1][C:32]([O:34][CH3:35])=[O:33])=[CH:7][CH:8]=[C:9]([Cl:11])[CH:10]=2)(=[O:24])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6586Methyl chloroformateHCID 183679133-Amino-2-benzoyl-4-chloro-1-(ethoxycarbonyl)indole

Product 1

HCID 69998691Ethyl 2-benzoyl-6chloro-3-[(methoxycarbonyl)amino]-1H-indole-1-caboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 3-amino-2-benzoyl-6-chloro-1H-indole-1-caboxylate (step 2, 1.5 g, 4.4 mmol) and pyridine (0.50 ml, 6.6 mmol) in dichloromethane (20 ml) was added methyl chloroformate (0.40 ml, 5.3 mmol) at room temperature. After stirring for 3 h, the mixture was poured into 2N aqueous HCl (20 ml) and extracted with dichloromethane (30 ml×2). The combined organic layers were dried (MgSO4) and concentrated to give 1.7 g (quant.) of the title compound as yellow amorphous solids.

Workup

  1. extractionextracted with dichloromethane (30 ml×2)
  2. dry with materialThe combined organic layers were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e3ffb8b046704cd18cae7894ae1e9c42
Source dataset
uspto-grants-2001_08
Patent number
US06277878B1

Reaction notes

Loading…