Sodium Hydroxide → HCID 59326812, compound

HRID 1880194Notes

Reaction equation

HRID 1880194 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[N:27]=[CH:26][CH:25]=[CH:24][C:18]=2[C:19]([O:21]CC)=[O:20])=[CH:14][CH:13]=1)=[O:11].[OH-].[Na+]>CO>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:13]=[CH:14][C:15]([O:16][C:17]2[N:27]=[CH:26][CH:25]=[CH:24][C:18]=2[C:19]([OH:21])=[O:20])=[CH:28][CH:29]=1)=[O:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59327218HCID 59327218, compound

Product 1

HCID 59326812HCID 59326812, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of ethyl 2-(4-(1H-benzo[d]imidazole-2-carbonyl)Phenoxy)nicotinate (12.0 g, 30.9 mmol) in methanol (100 mL) was added aqueous solution of NaOH (1.85 g, 46.3 mmol, 30 mL). The reaction mixture was heated up to reflux for 1 h. The reaction mixture was concentrated, diluted with water and filtered. The aqueous layer was washed with ethyl acetate and acidified by addition of 2N HCl to pH 6. The brown precipitate was collected by filtration, dried to give the title compound. MS (ESI, pos. ion) m/z: 360.1 (M+1).

Workup

  1. temperatureThe reaction mixture was heated up
  2. temperatureto reflux for 1 h
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with water
  5. filtrationfiltered
  6. washThe aqueous layer was washed with ethyl acetate
  7. additionacidified by addition of 2N HCl to pH 6
  8. filtrationThe brown precipitate was collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-ec88b6075c584c5c8ca1dadc16c1bb68
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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