Potassium Hydroxide → 3-(1-(Isopropylamino)phthalazin-6-yl)-4-methylbenzoic acid

HRID 2357536Notes

Reaction equation

HRID 2357536 reaction equation
[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[C:17]([CH:23]=[CH:24][C:25]=3[CH3:26])[C:18]([O:20]CC)=[O:19])=[CH:12][CH:13]=2)[CH:8]=[N:7][N:6]=1)([CH3:3])[CH3:2].[OH-].[K+]>C(O)C.O>[CH:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:16]=[C:17]([CH:23]=[CH:24][C:25]=3[CH3:26])[C:18]([OH:20])=[O:19])=[CH:12][CH:13]=2)[CH:8]=[N:7][N:6]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68453005Ethyl 3-(1-(isopropylamino)phthalazin-6-yl)-4-methylbenzoate

Product 1

HCID 684556533-(1-(Isopropylamino)phthalazin-6-yl)-4-methylbenzoic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A stirred solution of ethyl 3-(1-(isopropylamino)phthalazin-6-yl)-4-methylbenzoate (4 g, 11 mmol) (obtained by method D below) in ethanol/water (4:1) (50 mL) at RT was treated with potassium hydroxide (1 g, 23 mmol). The mixture was warmed to reflux and stirred for 2 h (M+1=322). The mixture was cooled to RT, then concentrated to remove the organic solvent. The mixture was diluted with 1 N aq. sodium hydroxide (20 mL), extracted with ether (2×50 mL). The combined ether extract was washed with 1N aq. sodium hydroxide (20 mL). The combined water layer was neutralized to pH 7 with conc. HCl. The white precipitate was collected and washed with water (20 mL), azotropically dried with toluene and placed under high vacuum to give 3-(1-(isopropylamino)phthalazin-6-yl)-4-methylbenzoic acid as pale yellow solid.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux
  3. concentrationconcentrated
  4. customto remove the organic solvent
  5. additionThe mixture was diluted with 1 N aq. sodium hydroxide (20 mL)
  6. extractionextracted with ether (2×50 mL)
  7. extractionThe combined ether extract
  8. washwas washed with 1N aq. sodium hydroxide (20 mL)
  9. customThe white precipitate was collected
  10. washwashed with water (20 mL)
  11. dry with materialazotropically dried with toluene

Sources & evidence

ORD record
ord-13ea86d2a6c24dc0b731d4bff8c3b6d7
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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