Lithium hydroxide, monohydrate → HCID 68979330, compound

HRID 349443Notes

Reaction equation

HRID 349443 reaction equation
C[O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[N:11]=[N:12][N:13]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=3)[N:14]=2)[CH:5]=1.O.[OH-].[Li+]>O1CCCC1>[CH3:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:13]2[N:12]=[N:11][C:10]([C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:24])=[O:2])=[N:14]2)=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 68980369HCID 68980369, compound

Product 1

HCID 68979330HCID 68979330, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The ester prepared in Step (b) (10.4 g, 0.032 mol) was suspended in aqueous tetrahydrofuran (20 mL, 1:1) followed by the addition of lithium hydroxide monohydrate (4 g, 0.096 mol) in one portion. Dissolution occurred after stirring at room temperature for 30 minute. The solution was stirred for an additional 16 hours. The THF was concentrated in vacuo and the aqueous solution was acidified to pH=1 using concentrated HCl. The resulting precipitate was collected by filtration and recrystallized from hexane/ethyl acetate to give the title compound (10 g, 100%) as a white solid. 1H NMR (DMSO-d6) δ 8.6 (s, 1H), 8.3 (d, 1H), 8.1 (d, 1H), 7.7 (t, 1H), 7.4 (d, 2H), 6.9 (d, 2H), 6.9 (s, 2H), 3.7 (s, 3H) ppm.

Workup

  1. dissolutionDissolution
  2. stirringThe solution was stirred for an additional 16 hours
  3. concentrationThe THF was concentrated in vacuo
  4. filtrationThe resulting precipitate was collected by filtration
  5. customrecrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-d922cc7a8f8d405e8157976385ab13e3
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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