Hydrochloric Acid → HCID 67850378, compound

HRID 2225442Notes

Reaction equation

HRID 2225442 reaction equation
[Cl-].[CH3:2][NH3+:3].C[Al](C)C.CO[C:10](=[O:26])[CH:11]=[C:12]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[N:25])=[CH:20][CH:19]=1)[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.Cl>C1(C)C=CC=CC=1>[CH3:2][NH:3][C:10](=[O:26])/[CH:11]=[C:12](\[C:18]1[CH:19]=[CH:20][C:21]([C:24]#[N:25])=[CH:22][CH:23]=1)/[N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11637Methanamine, hydrochloride (1:1)HCID 16682925TrimethylaluminumHCID 54412558HCID 54412558, compound

Product 1

HCID 67850378HCID 67850378, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

1.35 g of methylammonium chloride in 10 ml of toluene is mixed under argon with 7.5 ml of trimethylaluminum in 10 ml of toluene by instillation and stirred for 2 hours at room temperature. 50 mg of the E-methyl ester of example 1 is mixed in 2 ml of toluene with 2 ml of the above-produced reagent. It is stirred for 6 hours at 80° C., then mixed at room temperature with 1M hydrochloric acid and extracted with ether. The acid phase is alkalized with potassium carbonate and extracted with ethyl acetate. After washing with water and drying, the ethyl acetate phase is concentrated by evaporation. 30 mg of the title compound (50%) remains; melting range: 172°-180° C.

Workup

  1. stirringIt is stirred for 6 hours at 80° C.
  2. extractionextracted with ether
  3. extractionextracted with ethyl acetate
  4. washAfter washing with water
  5. customdrying
  6. concentrationthe ethyl acetate phase is concentrated by evaporation

Sources & evidence

ORD record
ord-2ce2e796e60b4956a3e4f71db79498f1
Source dataset
uspto-grants-1994_09
Patent number
US05344834

Reaction notes

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