Hydrochloric Acid → HCID 136050747, compound

HRID 1767342Notes

Reaction equation

HRID 1767342 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([O:18]C)=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[N:3]=1.Cl>[OH-].[Na+].C1COCC1.O>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][CH:12]([C:16]([OH:18])=[O:17])[CH2:11]2)[CH:5]=[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[OH:26])[N:3]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 135550587HCID 135550587, compound

Product 1

HCID 136050747HCID 136050747, compoundYield 72.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of methyl 3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]cyclo-hexanecarboxylate (151 mg, 0.43 mmol) in 2N NaOH (1 mL) and THF (2 mL) was stirred at 60° C. for 4 hrs. The reaction mixture was neutralized with 1N HCl (2 mL), and then diluted with water. The resulting precipitates were collected by filtration, washed with EtOH, and dried (60° C., 2 hrs, under reduced pressure) to give 3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]cyclohexanecarboxylic acid as a yellow solid (105 mg, yield; 72%).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with EtOH
  4. customdried (60° C., 2 hrs, under reduced pressure)

Sources & evidence

ORD record
ord-e33f1d36fe9446769deb801a42e07c31
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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