Diphenyl Ether → methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylate

HRID 441144Notes

Reaction equation

HRID 441144 reaction equation
[C:1]([NH:4][C:5]1[C:14]([Cl:15])=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[C:7]([O:16][CH2:17][C:18]#[CH:19])[CH:6]=1)(=[O:3])[CH3:2].O(C1C=CC=CC=1)C1C=CC=CC=1>>[C:1]([NH:4][C:5]1[C:6]2[CH:19]=[CH:18][CH2:17][O:16][C:7]=2[C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:13][C:14]=1[Cl:15])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 10588933Methyl 4-acetamido-5-chloro-2-(prop-2-yn-1-yloxy)benzoate

Product 1

HCID 54402287methyl 6-chloro-5-acetamido-2H-chromene-8-carboxylateYield 33.8%

Conditions

Temperature
230 °C

Procedure

A mixture of 40 parts of methyl 4-(acetylamino)-5-chloro-2-(2-propynoxy)benzoate and 172 parts of phenoxybenzene was stirred for 45 min. at 230° C. After cooling, the reaction mixture was poured into petroleumether. The organic layer was separated, dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3). The eluent of the desired fractions was evaporated and the residue was crystallized from acetonitrile, yielding 11.9 parts (33.8%) of methyl 5-(acetylamino)-6-chloro-2H-1-benzopyran-8-carboxylate (interm. 11).

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into petroleumether
  3. customThe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by column chromatography (silica gel; CH2Cl2 /CH3OH 97:3)
  8. customThe eluent of the desired fractions was evaporated
  9. customthe residue was crystallized from acetonitrile

Sources & evidence

ORD record
ord-464de602b62a40318145e82262907cbf
Source dataset
uspto-grants-1996_05
Patent number
US05521314

Reaction notes

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