Water → 2-Benzoyl-6-chloro-3-[(N,N-dimethylaminoacetyl)amino]indole

HRID 379817Notes

Reaction equation

HRID 379817 reaction equation
[C:1]([C:9]1[N:10](C(OCC)=O)[C:11]2[C:16]([C:17]=1[NH:18][C:19](=[O:22])[CH2:20]Cl)=[CH:15][CH:14]=[C:13]([Cl:23])[CH:12]=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:30][NH:31][CH3:32].O>CN(C=O)C>[C:1]([C:9]1[NH:10][C:11]2[C:16]([C:17]=1[NH:18][C:19](=[O:22])[CH2:20][N:31]([CH3:32])[CH3:30])=[CH:15][CH:14]=[C:13]([Cl:23])[CH:12]=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10473Dimethylamine, hydrochlorideHCID 183679602-Benzoyl-6-chloro-3-chloroacetylamino-1-(ethoxycarbonyl)indole

Product 1

HCID 183678312-Benzoyl-6-chloro-3-[(N,N-dimethylaminoacetyl)amino]indoleYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-benzoyl-6-chloro-3-(chloroacetylamino)-1-(ethoxycarbonyl)indole (step 1, 890 mg, 2.12 mmol) and dimethylamine hydrochloride (520 mg, 6.36 mmol) in DMF (30 ml) was stirred for 2 h. Water (80 ml) was added and the mixture extracted with an ethyl acetate-toluene mixture (2:1 v/v, 30 ml×2). The combined organic extracts were washed consecutively with water (50 ml) and brine (50 ml), dried (MgSO4) and evaporated. The residue was treated with a solution of 1N aqueous KOH (20 ml) and EtOH (40 ml) for 1 h, volatiles removed by evaporation and the residue extracted with ethyl acetate (30 ml×2). The combined organic extracts were dried (MgSO4) and evaporated. The crude product was recrystallized from ethyl acetate/hexane to give 350 mg (47%) of the title compound as a yellow solid. m.p.: 175-176° C. 1H-NMR (CDCl3) δ: 10.60 (1H, br s), 8.83 (1H, br s), 8.08 (1H, d, J=8.8 Hz), 7.88-7.70 (2H, m), 7.68-7.42 (3H, m), 7.29 (1H, d, J=1.8 Hz), 7.07 (1H, dd, J=1.8, 8.8 Hz), 3.04 (2H, s), 2.33 (6H, s)

Workup

  1. extractionthe mixture extracted with an ethyl acetate-toluene mixture (2:1 v/v, 30 ml×2)
  2. washThe combined organic extracts were washed consecutively with water (50 ml) and brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. additionThe residue was treated with a solution of 1N aqueous KOH (20 ml) and EtOH (40 ml) for 1 h
  6. customvolatiles removed by evaporation
  7. extractionthe residue extracted with ethyl acetate (30 ml×2)
  8. dry with materialThe combined organic extracts were dried (MgSO4)
  9. customevaporated
  10. customThe crude product was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-d5fe0b4fbe70478a91f28d9021442f24
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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