Ammonia → HCID 20335244, compound

HRID 1284359Notes

Reaction equation

HRID 1284359 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:14]([CH3:18])[C:15](O)=[O:16])[CH:8]=[CH:7]2.C(Cl)(=O)C(Cl)=O.[NH3:25]>C1C=CC=CC=1>[F:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH:10]=[C:9]([CH:14]([CH3:18])[C:15]([NH2:25])=[O:16])[CH:8]=[CH:7]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 65578Oxalyl chlorideHCID 20335242HCID 20335242, compound

Product 1

HCID 20335244HCID 20335244, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
0 °C

Procedure

A suspension of 2.4 g. of sodium hydride and 50 ml. of benzene is added to a mixture of 23 g. of 6-fluoro-2-naphthyl-α-methylacetic acid and 450 ml. of benzene. The resulting mixture is stirred for four hours. The mixture is cooled to 0°C and 19 g. of oxalyl chloride are added; after the addition, the mixture is allowed to stand for four hours. The resulting mixture is then saturated with ammonia and allowed to stand for eight hours. This mixture is then evaporated under reduced pressure. The residue is taken up in methylene chloride, washed with water to neutrality, dried, filtered, and evaporated to give 6-fluoro-2-naphthyl-α-methylacetamide.

Workup

  1. additionA suspension of 2.4 g
  2. additionafter the addition
  3. waitto stand for four hours
  4. waitto stand for eight hours
  5. customThis mixture is then evaporated under reduced pressure
  6. washwashed with water to neutrality
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-fe60bdd040a84801b37fb2e2f592371c
Source dataset
uspto-grants-1976_08
Patent number
US03978116

Reaction notes

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