Sodium Hydroxide → 5-(Hexyl{4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2-hydroxybenzoic acid

HRID 551949Notes

Reaction equation

HRID 551949 reaction equation
[CH2:1]([N:7]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]#[C:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)=[CH:24][CH:23]=1)[C:8]1[CH:20]=[CH:19][C:11]2[O:12]C(C)(C)[O:14][C:15](=[O:16])[C:10]=2[CH:9]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[OH-].[Na+]>CO>[CH2:1]([N:7]([CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]#[C:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)=[CH:26][CH:27]=1)[C:8]1[CH:20]=[CH:19][C:11]([OH:12])=[C:10]([CH:9]=1)[C:15]([OH:16])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 575545686-(hexyl{4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one

Product 1

HCID 160404755-(Hexyl{4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2-hydroxybenzoic acidYield 12%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-(hexyl{4-[(4-methoxyphenyl)ethynyl]benzyl}amino)-2,2-dimethyl-4H-1,3-benzodioxin-4-one (520 mg; 1.05 mmol) in MeOH (20 mL) was added an aqueous solution of NaOH (1.05 mL, 5N). The reaction mixture was stirred at rt for 1 h. The yellow precipitate obtained was filtrated and washed with cola water. It was suspended again in MeOH (20 mL) and aqueous solution of NaOH (2 mL, 5N) and heated at 70° C. overnight. The reaction mixture was poured into an aqueous solution of HCl (1N) and extracted with Et2O. The combined organic layers were washed with brine, dried over magnesium sulfate, filtrated and concentrated. Purification by preparative HPLC using a X-Terra column followed by a recrystallisation in MeOH gave 55 mg (12%) the title compound as a brown powder. HPLC, Rt: 4.24 min purity: 95.0%). LC/MS, M+(ESI): 458.3, M−(ESI): 456.1 1H NMR (CDCl3) δ: 12.70 (brs, 1H), 10.20 (brs, 1H), 7.46 (d, J=5.3 Hz, 2H), 7.44 (d, J=4.5 Hz, 2H), 7.23 (d, J=7.3 Hz, 2H), 6.98 (m, 4H), 6.78 (d, J=9.0 Hz, 1H), 4.46 (s, 2H), 3.78 (s, 3H), 3.31 (m, 2H), 1.51 (m, 2H), 1.25 (m, 6H), 0.84 (m, 3H).

Workup

  1. customThe yellow precipitate obtained
  2. filtrationwas filtrated
  3. washwashed with cola water
  4. temperatureaqueous solution of NaOH (2 mL, 5N) and heated at 70° C. overnight
  5. additionThe reaction mixture was poured into an aqueous solution of HCl (1N)
  6. extractionextracted with Et2O
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltrated
  10. concentrationconcentrated
  11. customPurification by preparative HPLC
  12. customfollowed by a recrystallisation in MeOH

Sources & evidence

ORD record
ord-00e4386d5dea43feb91c609397dac763
Source dataset
uspto-grants-2011_05
Patent number
US07947851B2

Reaction notes

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