Ethanol → HCID 18367903, compound

HRID 379903Notes

Reaction equation

HRID 379903 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([NH:23][C:24](=[O:27])[CH2:25][CH3:26])=[C:7]([C:11](=[O:22])[C:12]3[CH:17]=[C:16]([Cl:18])[CH:15]=[CH:14][C:13]=3[N+:19]([O-])=O)[NH:8]2)=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[NH2:19][C:13]1[CH:14]=[CH:15][C:16]([Cl:18])=[CH:17][C:12]=1[C:11]([C:7]1[NH:8][C:9]2[C:5]([C:6]=1[NH:23][C:24](=[O:27])[CH2:25][CH3:26])=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=2)=[O:22]

Participants

6

Reactant 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 18367904HCID 18367904, compound

Product 1

HCID 18367903HCID 18367903, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

A suspension of 6-chloro-2-(5-chloro-2-nitrobenzoyl)-3-(propionylamino)indole (step 3, 540 mg, 1.33 mmol), ammonium chloride (35.6 mg, 0.665 mmol), iron powder (391 mg, 6.65 mmol), ethanol (20 ml) and water (10 ml) was heated at reflux temperature for 1 h. After cooling to room temperature, the mixture was filtered through a pad of Celite. The filtrate was concentrated to give a crystalline residue. Purification by flash column chromatography eluting with ethyl acetate/hexane (1:3) afforded 394 mg (79%) of 2-(2-amino-5-chlorobenzoyl)-6-chloro-3-(propionylamino)indole. 1H-NMR (CDCl3) δ: 11.67 (1H, br s), 9.76 (1H, br s), 7.58 (1H, d, J=8.6 Hz), 7.43 (1H, d, J=1.5 Hz), 7.35 (1H, d, J=2.5 Hz), 7.26 (1H, dd, J=2.5, 8.9 Hz), 7.09 (1H, dd, J=1.8, 8.6 Hz), 6.99 (2H, br s), 6.83 (1H, d, J=8.9 Hz), 2.12 (2H, q, J=7.6 Hz), 0.90 (3H, t, J=7.6 Hz).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 h
  3. filtrationthe mixture was filtered through a pad of Celite
  4. concentrationThe filtrate was concentrated
  5. customto give a crystalline residue
  6. customPurification by flash column chromatography
  7. washeluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-cb43fa864fcc4a8ead8174ecc512d677
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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