Water → HCID 178524381, compound

HRID 906142Notes

Reaction equation

HRID 906142 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([O:14]C)=[O:13])[CH2:4][CH2:3]1.O1CCCC1.O.[OH-].[K+]>CO>[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][CH:18]=2)[C:12]([OH:14])=[O:13])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 178497927HCID 178497927, compound

Product 1

HCID 178524381HCID 178524381, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 3-[(trans-4-hydroxycyclohexyl)amino]benzoate (0.25 g, 1.00 mmol) in a mixture of methanol (20 mL), terahydrofuran (10 mL) and water (10 mL) was added a 4M aqueous solution of potassium hydroxide (0.5 mL, 2.00 mmol), and the reaction mixture was heated to reflux for five minutes. The organic portion of the solvent was evaporated, and the pH of the aqueous solution was adjusted to 2 by the addition of 2M aqueous hydrochloric acid. The aqueous mixture was partitioned with ethyl acetate, the organic layer was separated and washed with brine, dried over sodium sulfate, filtered, and the solution was concentrated to give 3-[(trans-4-hydroxycyclohexyl)amino]benzoic acid (40 mg, 17%). MS (EI) for C13H17NO3: 234 (M−H).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for five minutes
  3. customThe organic portion of the solvent was evaporated
  4. additionthe pH of the aqueous solution was adjusted to 2 by the addition of 2M aqueous hydrochloric acid
  5. customThe aqueous mixture was partitioned with ethyl acetate
  6. customthe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-f72590763aa54849a6476c6d9f2d9178
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

Loading…