Propionyl chloride → HCID 18367904, compound

HRID 379902Notes

Reaction equation

HRID 379902 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:23])[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].[C:24](Cl)(=[O:27])[CH2:25][CH3:26].[K+].[Br-]>>[Cl:11][C:7]1[CH:6]=[C:5]2[C:10]([C:2]([NH:1][C:24](=[O:27])[CH2:25][CH3:26])=[C:3]([C:12](=[O:23])[C:13]3[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=3[N+:20]([O-:22])=[O:21])[NH:4]2)=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 62324Propionyl chlorideHCID 253877Potassium BromideHCID 18367947HCID 18367947, compound

Product 1

HCID 18367904HCID 18367904, compound

Procedure

The title compound were prepared according to the procedure described in Example 19 from 3-amino-6-chloro-2-(5-chloro-2-nitrobenzoyl)indole (step 2) and propionyl chloride. m.p.: 245-246° C. IR (KBr) ν: 3078, 1665, 1628, 1580, 1526, 1497, 1340, 1313, 1238, 1022, 843 cm−1 1H-NMR (DMSO-d6) δ: 12.09 (1 H, br s), 9.26 (1 H, br s), 8.29 (1 H, d, J=8.7 Hz), 7.87 (1 H, dd, J=2.3, 8.7 Hz), 7.66 (1 H, d, J=2.0 Hz), 7.49 (1 H, d, J=8.6 Hz), 7.46 (1 H, d, J=2.0 Hz), 7.11 (1 H, dd, J=1.8, 8.7 Hz), 1.89 (2 H, q, J=7.9 Hz), 0.84 (3 H, t, J=7.9 Hz).

Sources & evidence

ORD record
ord-4d19fd6155e74c449702ec34d7b5a0ca
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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