HCID 86736409, compound → HCID 12909280, compound

HRID 614523Notes

Reaction equation

HRID 614523 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:13](C(O)=O)[N:12]2[C:7](=[CH:8][O:9][C:10]3[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=32)[N:6]=1)=[O:4]>C(Cl)(Cl)Cl>[CH:13]1[N:12]2[C:7]([CH2:8][O:9][C:10]3[CH:20]=[CH:19][CH:18]=[CH:17][C:11]=32)=[N:6][C:5]=1[C:3]([O:2][CH3:1])=[O:4]

Participants

3

Reactant 1

HCID 86736409HCID 86736409, compound

Product 1

HCID 12909280HCID 12909280, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

20 g (0.073 mole) of the 4H-2-methoxycarbonyl-imidazo-[2,1-c][1,4]-benzoxazine-1-carboxylic acid obtained in Step D were added to a flask provided with a magnetic stirrer and the flask was placed in an oil bath at 175°-80° C. Stirring was continued for about twenty minutes until effervescence ceased and the decarboxylated product thus formed was then dissolved in chloroform and the solution obtained was passed down a short silica column to remove any remaining low Rf impurities. The combined fractions containing methyl 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate were then evaported to dryness and ether was added with trituration. The offwhite product was filtered off, washed with a little ether and dried to obtain 14.0g (83% yield) of methyl 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate with a melting point of 133°-4° C.

Workup

  1. customprovided with a magnetic stirrer
  2. customthe flask was placed in an oil bath at 175°-80° C
  3. waitwas continued for about twenty minutes until effervescence
  4. customthe decarboxylated product thus formed
  5. customthe solution obtained
  6. customto remove any remaining low Rf impurities
  7. additionThe combined fractions containing methyl 4H-imidazo-[2,1-c][1,4]-benzoxazine-2-carboxylate
  8. additionwas added with trituration
  9. filtrationThe offwhite product was filtered off
  10. washwashed with a little ether
  11. customdried

Sources & evidence

ORD record
ord-917f2b3f855e402d9b2cdca937c33b9a
Source dataset
uspto-grants-1979_03
Patent number
US04145419

Reaction notes

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