Dimethylformamide → HCID 86728459, compound

HRID 570632Notes

Reaction equation

HRID 570632 reaction equation
P(Cl)(Cl)(Cl)=O.[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH2:17][CH2:18][CH3:19])=[CH:11]2.CN(C)[CH:22]=[O:23]>>[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([CH2:17][CH2:18][CH3:19])=[C:11]2[CH:22]=[O:23]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 10821490HCID 10821490, compound

Product 1

HCID 86728459HCID 86728459, compoundYield 86%

Procedure

Dimethylformamide (2 mL) was cooled to 0° C. Phosphorus oxychloride (0.5 mL) was added and the reaction mixture was stirred for 10 minutes. A solution of 5-methoxy-2-propylindole (325 mg, 1.7 mmol) in dimethylformamide (3 mL) was added to the reaction mixture dropwise over 10 minutes. The solution was stirred for an additional 40 minutes. The reaction mixture was added to ice cold 1 N NaOH (50 mL) and stirred for 10 minutes. The precipitate was collected and dried overnight in an oil driven vacuum pump equipped to a vacuum desiccator set at 40° C. yielding a white solid (318 mg, 86%): TLC Rf 0.67 in 4:1 ethyl acetate/hexanes. Melting point=166-168° C. 1H NMR (600 MHz, CDCl3) δ 10.16 (s, 1H), 8.31 (s, 1H), 7.79 (d, 1H, J=2.46 Hz), 7.23-7.22 (d, 1H, J=8.82 Hz), 6.89-6.87 (dd, 1H, J1=2.54, J2=8.76 Hz), 3.89 (s, 3H), 3.06-3.04 (t, 2H, J=7.5 Hz), 1.84-1.80 (m, 2H) 1.05-1.03 (t, 3H, J=7.32 Hz); 13C NMR (150 MHz, CDCl3) δ 184.4, 156.5, 151.4401, 129.6, 126.7, 114.7, 113.5, 111.5, 103.0, 55.8, 28.3, 23.5, 13.8. Elemental analysis calculated for C13H15NO2: C, 71.87; H, 6.96; N, 6.45. Found: C, 71.92; H, 6.97; N, 6.34.

Workup

  1. stirringThe solution was stirred for an additional 40 minutes
  2. stirringstirred for 10 minutes
  3. customThe precipitate was collected
  4. customdried overnight in an oil
  5. customequipped to a vacuum desiccator
  6. customset at 40° C.

Sources & evidence

ORD record
ord-4584cb5850e64ecc913a7bdcac27d38d
Source dataset
uspto-grants-2015_05
Patent number
US09023871B2

Reaction notes

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