Hydrochloric Acid → HCID 57722984, compound

HRID 1987036Notes

Reaction equation

HRID 1987036 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C[Al](C)C.C1(C)C=CC=CC=1.[Cl:20][C:21]1[C:26]([CH2:27][CH2:28][C:29](OC)=[O:30])=[C:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=2[Cl:39])[CH:24]=[C:23]([Cl:40])[N:22]=1.Cl>ClCCl.O>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:29](=[O:30])[CH2:28][CH2:27][C:26]1[C:21]([Cl:20])=[N:22][C:23]([Cl:40])=[CH:24][C:25]=1[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[Cl:39]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 72402-ChloroanilineHCID 16682925TrimethylaluminumHCID 57722978HCID 57722978, compound

Product 1

HCID 57722984HCID 57722984, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-Chloroaniline (0.87 ml, 8.21 mmol) in dichloromethane (80 ml) was treated with 2M trimethylaluminium in toluene (4.1 ml, 8.2 mmol) at 0-5° under nitrogen. After stirring for 15 min. a solution of methyl 3-[2,6-dichloro-4-(2-chlorophenyl)-3-pyridinyl]propanoate (1.40 g, 4.063 mmol) in dichloromethane (40 ml) was added and the solution stirred at 21° for 17 h. Water (15 ml) was added (very slowly at first), followed by sufficient 2M hydrochloric acid to dissolve all the precipitated aluminium salts. The organic phase was separated and the aqueous phase further extracted with dichloromethane (50 ml). The combined organic extracts passed through a hydrophobic frit, evaporated in vacuo, and the oily residue purified by column chromatography over silica (70 g) eluting with cyclohexane-ethyl acetate (100:0-65:35) to afford the title compound as a gum (1.52 g, 85%).

Workup

  1. additionwas added
  2. customThe organic phase was separated
  3. extractionthe aqueous phase further extracted with dichloromethane (50 ml)
  4. customevaporated in vacuo
  5. customthe oily residue purified by column chromatography over silica (70 g)
  6. washeluting with cyclohexane-ethyl acetate (100:0-65:35)

Sources & evidence

ORD record
ord-53d3b07ad5974f3ba7e0cd7603bcd0c8
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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