Pyridine → HCID 10524870, compound

HRID 2228547Notes

Reaction equation

HRID 2228547 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([O:11][Si:12]([CH3:18])([CH3:17])[C:13]([CH3:16])([CH3:15])[CH3:14])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].N1C=CC=CC=1.[C:25]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30](Cl)=[O:31])#[N:26]>C(Cl)Cl>[C:25]([C:27]1[CH:28]=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30]([NH:6][C:5]1[CH:7]=[CH:8][C:9]([O:11][Si:12]([CH3:17])([CH3:18])[C:13]([CH3:14])([CH3:15])[CH3:16])=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2])=[O:31])#[N:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 3084833-Cyanobenzoyl chlorideHCID 120422994-(Tert-butyldimethylsilyl)oxy-2-nitroaniline

Product 1

HCID 10524870HCID 10524870, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 2-nitro-4-(dimethyl-t-butylsiloxy)aniline (10.01 g, 37.30 mmol) and CH2Cl2 (400 mL) at 0° C was added pyridine (3.4 mL, 42.0 mmol) followed by the 3-cyanobenzoyl chloride (8.65 g, 52.2 mmol). The reaction was allowed to warm to room temperature and stirred for 1 h. The reaction was diluted with CH2Cl2 (800 mL) and washed with sat. aq. NH4Cl (2×200 mL). The organic layer was MgSO4 dried, filtered, and concentrated. The residue was chromatographed (20% EtOAc/hexanes) to give the title compound as a solid (13.94 g, 94%); IR(CHCl3): 2932, 1689, 1508, 1289, 863 cm−1; NMR(300 MHz, CDCl3): δ0.27 (s, 6H), 1.02 (s, 9H), 7.27 (s, 1H), 7.70 (m, 2H), 7.90 (d, J=7.8, 1H), 8.16 (d, J=1.2, 1H), 8.30 (s, 1H), 8.79 (d, J=9.3, 1H), 11.15 (br s, 1H); MS(FD): 397.0.

Workup

  1. washwashed with sat. aq. NH4Cl (2×200 mL)
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7b183db3cf9f422ca5f650a184c903a4
Source dataset
uspto-grants-2002_07
Patent number
US06417200B1

Reaction notes

Loading…