Ammonia → HCID 18670595, compound

HRID 1059386Notes

Reaction equation

HRID 1059386 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH3:21])([CH3:20])[C:15](OCC)=[O:16])=[N:8][CH:9]=1)([O-:3])=[O:2].[N+:22](C1C=CC(CCCCC(C)(C)C(O)=O)=NC=1)([O-])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.N.[Cl-].[Na+]>O1CCCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][C:14]([CH3:21])([CH3:20])[C:15]([NH2:22])=[O:16])=[N:8][CH:9]=1)([O-:3])=[O:2]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 5234Sodium ChlorideHCID 682631,1'-CarbonyldiimidazoleHCID 17781958HCID 17781958, compoundHCID 18670448HCID 18670448, compound

Product 1

HCID 18670595HCID 18670595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 6-(5-nitropyridin-2-yl)-2,2-dimethylhexanoate was treated in the same manner as the one of Example 18 and 661 mg of 6-(5-nitropyridin-2-yl)-2,2-dimethylhexanoic acid thus obtained was dissolved in 15 ml of tetrahydrofuran. After adding 695 mg of carbonyldiimidazole, the resulting mixture was heated under reflux for 2 hours. Then the reaction mixture was cooled to room temperature and 25 ml of saturated aqueous ammonia was added thereto followed by stirring over day and night. After the completion of the reaction, the reaction mixture was poured into a saturated aqueous solution of sodium chloride and repeatedly extracted with ethyl acetate. The extracts were dried over anhydrous sodium sulfate and filtered. The filtrate was distilled under reduced pressure and the residue was purified by silica gel column chromatography (eluted with toluene/acetone) to thereby give 453 mg of the title compound as white crystals.

Workup

  1. customthus obtained
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 2 hours
  4. customAfter the completion of the reaction
  5. extractionrepeatedly extracted with ethyl acetate
  6. dry with materialThe extracts were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. distillationThe filtrate was distilled under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluted with toluene/acetone)

Sources & evidence

ORD record
ord-8cb46ba10097445a87667ec89682b515
Source dataset
uspto-grants-2003_02
Patent number
US06518423B1

Reaction notes

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