Hydrochloric Acid → 4-[(3-Nitro-4-pyridyl)oxy]cyclohexanecarboxylic acid

HRID 524936Notes

Reaction equation

HRID 524936 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:16][CH2:15][CH:14]([C:17]([O:19]C)=[O:18])[CH2:13][CH2:12]1)([O-:3])=[O:2].O.NC1C(C(ON2C3C=CC=CC=3N=N2)=O)=C2N=CC(CC#N)=CN2N=1.Cl>C1COCC1.C(OCC)(=O)C.CO>[N+:1]([C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[O:10][CH:11]1[CH2:12][CH2:13][CH:14]([C:17]([OH:19])=[O:18])[CH2:15][CH2:16]1)([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 86720995Methyl 4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxylateHCID 901998921H-benzo[d][1,2,3]triazol-1-yl 2-amino-6-(cyanomethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 867209944-[(3-Nitro-4-pyridyl)oxy]cyclohexanecarboxylic acid

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxylate (250.0 mg, 0.8920 mmol) (prepared according to methods similar to the one depicted in Step 1 of preparation O-1) in THF (2.748 mL), Water (2.748 mL) and MeOH (1.5 mL) solution was stirred at RT and treated with Lithium hydroxide monohydrate (Water (1)) (224.6 mg, 5.352 mmol). The mixture was stirred at RT overnight, then was concentrated under reduced pressure to remove the organics. The aqueous solution was cooled in an ice bath then acidified with HCl (5.352 mL of 1 M, 5.352 mmol) to pH 4-5. Ethyl acetate was then added and the layers separated. Aqueous layer was extracted further with ethyl acetate (2×5 mL) and the combined organic layers were dried over MgSO4 and concentrated in vacuo to leave the 4-[(3-nitro-4-pyridyl)oxy]cyclohexanecarboxylic acid as a yellow oil. Used in the next step without further purification. MS (ES+) 267.0.

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customto remove the organics
  3. temperatureThe aqueous solution was cooled in an ice bath
  4. customthe layers separated
  5. extractionAqueous layer was extracted further with ethyl acetate (2×5 mL)
  6. dry with materialthe combined organic layers were dried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca59a474999b410bb27219791ca4c293
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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