Ammonia → HCID 54202893, compound

HRID 1088461Notes

Reaction equation

HRID 1088461 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:23]=[CH:24][CH:25]=3)[O:17][CH:18]([CH3:22])[C:19](O)=[O:20])=[N:9]2)=[CH:4][CH:3]=1.C([N:28](CC)CC)C.ClC(OCC)=O.N>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([CH:23]=[CH:24][CH:25]=3)[O:17][CH:18]([CH3:22])[C:19]([NH2:28])=[O:20])=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 54478688HCID 54478688, compound

Product 1

HCID 54202893HCID 54202893, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

(+)-2-(3-(2-(7-Chloroquinolin-2-yl)ethenyl)phenoxy)propanoic acid from Example 72 (2.372 g, 6.71 mmol) was dissolved in methylene chloride (40 mL) containing triethylamine (1.87 mL, 12.5 mmol), and ethyl chloroformate (710 μL, 7.38 mmol) in methylene chloride (20 mL) was added dropwise at -15° C. with stirring. The mixture was stirred for a further 20 minutes at -15° C., and then it was poured into methylene chloride (125 mL) that had been saturated with ammonia at 0° C. The reaction mixture was stirred for a few minutes, and then poured into ice-water The mixture was filtered, and the filtrate was separated. Evaporation of the methylene chloride layer gave more solid, and the two fractions were combined and recrystallized from acetonitrile to give the title product, mp 195°-197° C., [α]D -9.8° (c 0.515 in dimethylformamide).

Workup

  1. additionwas added dropwise at -15° C.
  2. stirringThe mixture was stirred for a further 20 minutes at -15° C.
  3. stirringThe reaction mixture was stirred for a few minutes
  4. filtrationwas filtered
  5. customthe filtrate was separated
  6. customEvaporation of the methylene chloride layer
  7. customgave more solid
  8. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-98c5ec1a52434ea39ad60ed46a0601c9
Source dataset
uspto-grants-1990_10
Patent number
US04962203

Reaction notes

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