Sodium Hydroxide → HCID 85059182, compound

HRID 2099988Notes

Reaction equation

HRID 2099988 reaction equation
Cl.[NH2:2][OH:3].[OH-].[Na+].C[O:7][C:8](=O)[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18](=[O:27])[CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=1>CO.O>[OH:3][NH:2][C:8](=[O:7])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([NH:17][C:18](=[O:27])[CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:12]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 66958338HCID 66958338, compound

Product 1

HCID 85059182HCID 85059182, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of hydroxylamine hydrochloride (0.14 g, 2.01 mmol) (Acros) in methanol (2.0 ml) a solution of NaOH (0.16 g, 4.00 mmol) in H2O (0.2 ml) was added and the resultant mixture was stirred at ambient temperature for 5 min. To the reaction mixture a 3-[3-(3-phenylacryloylamino)-phenyl)-acrylic acid methyl ester (8) (0.15 g, 0.49 mmol) solution in methanol (2.0 ml) was added and stirred at ambient temperature for 1.5 hour. The reaction mixture was partitioned between ethyl acetate and 2N HCl. The organic layer was washed successively with water and saturated NaCl, and the solvent was removed. The residue was crystallized from ethyl acetate-methanol giving pure title compound (0.040 g, 26%), m.p. 178° C. 1H NMR (DMSO-d6, HMDSO), δ: 6.45 (d, 1H, J=16.0 Hz); 6.85 (d, 1H, J=16.0 Hz); 7.14-7.76 (m, 10 H); 8.00 (br s, 1H); 9.03 (br s, 1H); 10.32 (br s, 1H); 10.83 (br s, 1H). HPLC analysis on Zorbax SB-C18 column: impurities 4.5% (column size 4.6×150 mm; mobile phase acetonitrile−0.1% H3PO4, gradient from 30 to 100%; sample concentration 0.25 mg/ml; flow rate 1.5 ml/min; detector: UV 270 nm). Anal. Calcd for C18H16N2O3×0.25 H2O, %: C, 69.11; H, 5.32; N, 8.95. Found, %: C, 69.09; H, 5.06; N, 8.81.

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and 2N HCl
  3. washThe organic layer was washed successively with water and saturated NaCl
  4. customthe solvent was removed
  5. customThe residue was crystallized from ethyl acetate-methanol giving pure title compound (0.040 g, 26%), m.p. 178° C

Sources & evidence

ORD record
ord-355709f00f444f9aa2a7f4b339a210ac
Source dataset
uspto-grants-2009_08
Patent number
US07569724B2

Reaction notes

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