Ammonium Chloride → HCID 22622206, compound

HRID 840109Notes

Reaction equation

HRID 840109 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-])=O)=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[CH:15]([Mg]Br)=[CH2:16].[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:16]=[CH:15][NH:12][C:5]2=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2524448-Chloro-5-nitroquinolineHCID 178418507HCID 178418507, compound

Product 1

HCID 22622206HCID 22622206, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 8-chloro-5-nitroquinoline (5.0 g, 24 mmol) in tetrahydrofuran (70 mL) at −78° C. under Ar was added a solution of vinylmagnesium bromide (1.0 M in tetrahydrofuran, 72 mL, 72 mmol) over 5 min. The mixture was stirred for 40 minutes, poured into aqueous ammonium chloride solution (200 mL) and extracted with ether (3×100 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; ethyl acetate-heptane (1:1)] to give 5-chloro-1H-pyrrolo[2,3-f]quinoline as an orange solid (1.0 g, 21%): mp 248-250° C.; IR νmax (Nujol)/cm−1 3198, 2924, 2854, 1500, 1465, 1377, 1364, 1290, 1162, 1126, 1085, 949, 887, 810, 780, 744, 706, 633, 599 and 512; NMR δH (400 Mz, CDCl3) 6.64 (1H, d, J 3 Hz) 7.56 (1H, t, J 4 Hz) 7.65 (1H, dd, J2.5, 8.5 Hz) 8.14 (1H, s) 8.83 (1H, d, J 8.5 Hz) 8.88 (1H, d, J 2.5 Hz) 12.37 (1H, m).

Workup

  1. extractionextracted with ether (3×100 mL)
  2. washThe combined organic extracts were washed (water, brine)
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography [SiO2; ethyl acetate-heptane (1:1)]

Sources & evidence

ORD record
ord-ba7b4f9efdf8464e951c1b0448adcbc1
Source dataset
uspto-grants-2002_04
Patent number
US06365598B1

Reaction notes

Loading…