Oxalyl chloride → HCID 14877952, compound

HRID 1460335Notes

Reaction equation

HRID 1460335 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[C:9]([N:13]2[CH:17]=[N:16][N:15]=[N:14]2)[C:10](O)=[O:11])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1C=CC=CC=1.N1C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[C:9]([N:13]2[CH:17]=[N:16][N:15]=[N:14]2)[CH2:10][OH:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 14877951HCID 14877951, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14877952HCID 14877952, compoundYield 88.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 241BenzeneSolvent

Conditions

Temperature
-80 °C

Procedure

The crude acid from Step A was suspended in 12 mL of dry benzene and the mixture was treated with 350 mL of oxalyl chloride. To this suspension was added one drop of pyridine and a very vigorous reaction was apparent. The clear homogenous solution was warmed to-reflux temperature for 10 minutes then kept at about 70° C. for 2 days under an argon atmosphere. Most of the solvents were evaporated under high vacuum and the semi-solid was dissolved in 6 mL of tetrahydrofuran. To this chilled (-80° C., dry ice-acetone) solution under argon was added dropwise 0.5 mL (0.5 mmole, 1.0 M in tetrahydrofuran) of lithium aluminum hydride and the reduction was complete in one hour. The crude reaction mixture was quenched with 2.0 M HCl and the organic residue was extracted with ethyl acetate, dried and evaporated to give 0.21 g (88.7%) of the title compound which was pure enough to be used in the next step.

Workup

  1. customa very vigorous reaction
  2. temperatureThe clear homogenous solution was warmed
  3. temperatureto-reflux temperature for 10 minutes
  4. customMost of the solvents were evaporated under high vacuum
  5. dissolutionthe semi-solid was dissolved in 6 mL of tetrahydrofuran
  6. waitthe reduction was complete in one hour
  7. customThe crude reaction mixture
  8. customwas quenched with 2.0 M HCl
  9. extractionthe organic residue was extracted with ethyl acetate
  10. customdried
  11. customevaporated

Sources & evidence

ORD record
ord-46e7e7849f8c45eea90a603c571006f9
Source dataset
uspto-grants-1991_12
Patent number
US05070206

Reaction notes

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