2-Methoxyethylamine → 6-bromo-4-(2-methoxyethylamino)-3-propyl-2H-1-benzopyran-2-one

HRID 1636436Notes

Reaction equation

HRID 1636436 reaction equation
C(N(CC)CC)C.[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[C:15]([CH2:19][CH2:20][CH3:21])=[C:14](Cl)[C:13]=2[CH:23]=1.[CH3:24][O:25][CH2:26][CH2:27][NH2:28]>C(O)C>[Br:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C:16](=[O:18])[C:15]([CH2:19][CH2:20][CH3:21])=[C:14]([NH:28][CH2:27][CH2:26][O:25][CH3:24])[C:13]=2[CH:23]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 8471TriethylamineHCID 193516286-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one

Product 1

HCID 193516116-bromo-4-(2-methoxyethylamino)-3-propyl-2H-1-benzopyran-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine was added to a solution of 6-bromo-4-chloro-3-propyl-2H-1-benzopyran-2-one (0.5 g), in dry ethanol (10 ml) followed by 2-methoxyethylamine (0.16 ml). The mixture was heated at reflux under nitrogen overnight, evaporated and the residue extracted with ethyl acetate and the extract washed with dilute hydrochloric acid, brine, dried and evaporated under reduced pressure. The residue was triturated with ethanol and light petroleum (b.p. 40-60° C.) to give 6-bromo-4-(2-methoxyethylamino)-3-propyl-2H-1-benzopyran-2-one, m.p. 75-7° C. (compound 21).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under nitrogen overnight
  3. customevaporated
  4. extractionthe residue extracted with ethyl acetate
  5. washthe extract washed with dilute hydrochloric acid, brine
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was triturated with ethanol and light petroleum (b.p. 40-60° C.)

Sources & evidence

ORD record
ord-f26ce42f4add470c89c8f53035856487
Source dataset
uspto-grants-2000_03
Patent number
US06034121

Reaction notes

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