Methanol → HCID 67086961, compound

HRID 243881Notes

Reaction equation

HRID 243881 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#N)=[C:5]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1.[OH-:17].[Na+].C[OH:20]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]([OH:20])=[O:17])=[C:5]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[CH:4]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 67117244HCID 67117244, compound

Product 1

HCID 67086961HCID 67086961, compound

Procedure

4-Methoxy-2-(pyrimidin-2-yl)benzonitrile (85 mg, 0.4 mmol) was dissolved in MeOH (20 mL) was treated with 2M aq NaOH (15 mL). The reaction was heated at reflux overnight, the reaction was cooled to room temperature and filtered to remove the solids and washed with cold MeOH. The filtrate was concentrated to minimum volume and then acidified to pH=3 with 6 N aq. HCl and cooled to 0° C. then filtered and washed with cold water. This material was used crude in subsequent reactions.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. filtrationfiltered
  4. customto remove the solids
  5. washwashed with cold MeOH
  6. concentrationThe filtrate was concentrated to minimum volume
  7. temperaturecooled to 0° C.
  8. filtrationthen filtered
  9. washwashed with cold water

Sources & evidence

ORD record
ord-345510a82f664e9ba855205c47f31ee8
Source dataset
uspto-grants-2014_02
Patent number
US08653263B2

Reaction notes

Loading…