Ammonium Chloride → HCID 21082692, compound

HRID 347436Notes

Reaction equation

HRID 347436 reaction equation
Br[C:2]1[CH:3]=[C:4]2[O:27][CH2:26][O:25][C:5]2=[C:6]([CH:24]=1)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]=[CH:10][C:9]=1[C:22]#[N:23].[CH2:28]([O:31][CH3:32])[C:29]#[CH:30].N1CCCC1.[Cl-].[NH4+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:22]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[NH:7][C:6]1[CH:24]=[C:2]([C:30]#[C:29][CH2:28][O:31][CH3:32])[CH:3]=[C:4]3[O:27][CH2:26][O:25][C:5]=13)=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)#[N:23]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 31268PyrrolidineHCID 693933-MethoxypropyneHCID 17980573HCID 17980573, compound

Product 1

HCID 21082692HCID 21082692, compoundYield 21.9%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(5-bromo-2,3-methylenedioxyanilino)-3-cyano-6,7-dimethoxyquinoline (0.15 g), methyl 2-propynyl ether (0.049 g), tetrakis(triphenylphosphine)palladium(0) (0.02 g) and pyrrolidine (2 ml) was stirred and heated to 80° C. for 8 hours. The resultant mixture was cooled to ambient temperature, poured into a dilute aqueous ammonium chloride solution and extracted with ethyl acetate. The organic phase was washed with water and with a saturated brine solution, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and methanol as eluent. There was thus obtained the title compound as a solid (0.032 g); NMR Spectrum: (CDCl3) 3.4 (s, 3H), 3.77 (s, 3H), 4.04 (s, 3H), 4.24 (s, 2H), 5.97 (s, 2H), 6.65 (br s, 1H), 6.73 (d, 1H), 6.78 (d, 1H), 6.99 (s, 1H), 7.38 (s, 1H), 8.63 (s, 1H); Mass Spectrum: M+H+ 418.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water and with a saturated brine solution
  3. dry with materialdried over magnesium sulphate
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica using
  6. temperatureincreasingly polar mixtures of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-f356203fead842808ca609c28a41208e
Source dataset
uspto-grants-2007_02
Patent number
US07173135B2

Reaction notes

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