Nitromethane → HCID 66765892, compound

HRID 341283Notes

Reaction equation

HRID 341283 reaction equation
C([O-])(=O)C.[NH4+].[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([CH:24]=O)=[CH:21][CH:22]=3)[C:17]3[CH:26]=[C:27]([Cl:30])[CH:28]=[N:29][C:16]2=3)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[N+:31]([CH3:34])([O-:33])=[O:32]>>[C:6]1([S:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([CH:24]=[CH:34][N+:31]([O-:33])=[O:32])=[CH:21][CH:22]=3)[C:17]3[CH:26]=[C:27]([Cl:30])[CH:28]=[N:29][C:16]2=3)(=[O:14])=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 58514557HCID 58514557, compound

Product 1

HCID 66765892HCID 66765892, compoundYield 89.5%

Procedure

Solid ammonium acetate (121 mg, 1.1 equiv. 1.56 mmol) was added to solution of 9-benzenesulfonyl-3-chloro-9H-pyrido[2,3-b]indole-6-carbaldehyde (524 mg, 1.42 mmol) in nitromethane (5.5 mL). The mixture was vigorously stirred and boiled at 100° C. for 2 h. Then the mixture was cooled in an ice bath and concentrated under reduced pressure. Trituration of the crude residue from ethanol followed by filtration afforded 14 (528 mg, 89.5%), 1H-NMR (300 MHz, CDCl3): δ 8.81 (d, 1H, J=1.6 Hz), 8.70 (d, 1H, J=2.3 Hz), 8.65 (d, 1H, J=2.3 Hz), 8.42 (d, 1H, J=8.8 Hz), 8.25 (s, 2H), 8.17 (dd, 1H, J=1.6, 8.9 Hz), 8.09 (d, 1H, J=7.2 Hz), 8.09 (d, 1H, J=8.8 Hz), 7.71 (t, 1H, J=7.4 Hz), 7.60 (d, 1H, J=8.1 Hz), 7.58 (t, 1H, J=7.4 Hz); 13C-NMR (75 MHz, DMSO-d6): δ 148.7 (C), 146.0 (CH), 139.4 (C), 138.7 (CH), 137.9 (CH), 137.3 (C), 135.2 (CH), 130.9 (CH), 129.8 (2 CH), 129.5 (CH), 127.3 (C), 127.1 (2 CH), 126.5 (C), 123.8 (CH), 122.2 (C), 118.9 (C), 115.0 (CH), MS (ESI) m/z 414 [M+H+]

Workup

  1. temperatureThen the mixture was cooled in an ice bath
  2. concentrationconcentrated under reduced pressure
  3. filtrationTrituration of the crude residue from ethanol followed by filtration

Sources & evidence

ORD record
ord-ac008542e40c40c0bd84f7f14a2516cd
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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