Hydrochloric Acid → HCID 178472338, compound

HRID 452534Notes

Reaction equation

HRID 452534 reaction equation
[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[C:13](N)=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[ClH:19].N([O-])=O.[Na+]>[Cu]Cl>[CH2:1]([O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[C:13]([Cl:19])=[N:14][CH:15]=[CH:16][CH:17]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 178472340HCID 178472340, compound

Product 1

HCID 178472338HCID 178472338, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

To a solution of trans-4-(2-amino-pyridin-3-yl)-cyclohexanecarboxylic acid ethyl ester (0.21 g, 0.86 mmol) in concentrated hydrochloric acid (3.7 ml, 43 mmol) was added solid sodium nitrite (1.49 g, 21.5 mmol) at 0-5° C. The cooling bath was removed and copper(I) chloride (3.58 g, 36.2 mmol) was added at room temperature. After stirring for 2 h the mixture was partitioned between water (50 ml) and ethyl acetate (50 ml). The organic layer was collected. The aqueous layer was extracted with two 50-ml portions of ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate and concentrated to dryness. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.093 g, 44%) as yellow oil. MS m/e: 268 ([M+H]+)

Workup

  1. customThe cooling bath was removed
  2. customwas partitioned between water (50 ml) and ethyl acetate (50 ml)
  3. customThe organic layer was collected
  4. extractionThe aqueous layer was extracted with two 50-ml portions of ethyl acetate
  5. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0a89993d59684486bb19296ab5701f52
Source dataset
uspto-grants-2013_07
Patent number
US08492376B2

Reaction notes

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