Aniline → HCID 20205108, compound

HRID 978106Notes

Reaction equation

HRID 978106 reaction equation
[OH:1][C:2]1[C:7]2[C:8]([CH3:14])=[C:9]([C:11]([OH:13])=O)[O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[C:16]([O:18][CH2:19]C)=[O:17].C(N(CC)CC)C.[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)Cl>[C:29]1([NH:28][C:11]([C:9]2[O:10][C:6]3[CH:5]=[CH:4][CH:3]=[C:2]([O:1][C:16]([O:18][CH3:19])=[O:17])[C:7]=3[C:8]=2[CH3:14])=[O:13])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 94976624-Hydroxy-3-methyl-1-benzofuran-2-carboxylic acid

Product 1

HCID 20205108HCID 20205108, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of 4-hydroxy-3-methylbenzofuran-2-carboxylic acid (1.12 g, 6 mmole), ethyl chloroformate (1.01 ml, 13.2 mmole), and methylene chloride (20 ml) stirred at 0°-5° C. under argon was added triethylamine (1.82 ml, 13.2 mmole) in methylene chloride (6 ml) dropwise over 5 minutes. The mixture was stirred for 15 minutes and then aniline (1.11 mg, 12 mmole) was added followed by the dropwise addition of triethylamine (1.82 ml, 13.2 mmole) in methylene chloride (3 ml). After 30 minutes, the reaction mixture was washed with water, dried with MgSO4 and evaporated to dryness. The crude product was purified by column chromatography (70 g of Merck silica gel eluted with 1:1:3 ethyl acetate/methylene chloride/hexane to yield 1.38 g (68.1%) of product.

Workup

  1. stirringThe mixture was stirred for 15 minutes
  2. washthe reaction mixture was washed with water
  3. dry with materialdried with MgSO4
  4. customevaporated to dryness
  5. customThe crude product was purified by column chromatography (70 g of Merck silica gel
  6. washeluted with 1:1:3 ethyl acetate/methylene chloride/hexane

Sources & evidence

ORD record
ord-e7f067c8daf64976837c3bff49091309
Source dataset
uspto-grants-1987_05
Patent number
US04663347

Reaction notes

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