Methanol → HCID 67086961, compound

HRID 1524941Notes

Reaction equation

HRID 1524941 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-160def103b2041f389aed85e4b6ab51e
Source dataset
uspto-grants-2015_07
Patent number
US09079911B2

Reaction notes

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