Propionyl chloride → 5-Chloro-2-(3-chlorobenzoyl)-3-(propionylamino)indole

HRID 379798Notes

Reaction equation

HRID 379798 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([Cl:11])[CH:9]=2)[N:4](C(OCC)=O)[C:3]=1[C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1.[C:26](Cl)(=[O:29])[CH2:27][CH3:28]>C(OCC)(=O)C>[Cl:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3]([C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)=[C:2]2[NH:1][C:26](=[O:29])[CH2:27][CH3:28]

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 183677413-Amino-5-chloro-2-(3-chlorobenzoyl)-1-(ethoxycarbonyl)indole

Product 1

HCID 183677635-Chloro-2-(3-chlorobenzoyl)-3-(propionylamino)indole

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared according to the procedure described in Example 2 (Method A) from 3-amino-5-chloro-2-(3-chlorobenzoyl)-1-(ethoxycarbonyl)indole (step 1) and propionyl chloride. m.p.: 206.5-207.5° C. (ethyl acetate) 1H-NMR (CDCl3) δ: 9.78 (1H, br s), 8.31 (1H, s), 8.28 (1H, br s), 7.78 (1H, s), 7.70-7.59 (2H, m), 7.51 (1H, t, J=8 Hz), 7.34 (1H, dd, J=8, 1.5 Hz), 7.25 (1H, d, J=8 Hz), 2.51 (2H, q, J=7 Hz), 1.30 (3H, t, J=7 Hz)

Sources & evidence

ORD record
ord-7888b38784bb445fb7ee0989c030d8d9
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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