Hydroxylamine → HCID 9901787, compound

HRID 1362559Notes

Reaction equation

HRID 1362559 reaction equation
C[O:2][C:3](=O)[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1.[NH2:25][OH:26].C[O-].[Na+]>CO>[OH:26][NH:25][C:3](=[O:2])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13](=[O:23])[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 10942334Sodium MethoxideHCID 66958346HCID 66958346, compound

Product 1

HCID 9901787HCID 9901787, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(Method G6) To a mixture of 3-[3-(4-phenyl-butyrylamino)-phenyl]acrylic acid methyl ester (3d) (0.323 g, 1.0 mmol) and hydroxylamine (0.278 g, 4.0 mmol) in methanol (7 ml) a 3.43 N solution of sodium methylate (1.75 ml, 6.0 mmol) in methanol was added. The resulting mixture was stirred at ambient temperature for 7 hours, diluted with saturated NaH2PO4 (50 ml) and extracted with ethyl acetate (3×25 ml). The organic layer was washed with saturated NaCl and dried (Na2SO4). The solvent was evaporated and the residue was crystallized from acetonitrile affording the title compound as reddish crystals (0.122 g, 38%). M.p. 152-153° C. (from acetonitrile). 1H NMR (DMSO-d6, HMDSO) δ: 1.69-2.11 (m, 2H); 2.35 (t, 2H, J=7.4 Hz); 2.64 (t, 2H, J=7.0 Hz); 6.45 (d, 1H, J=15.6 Hz); 7.12-7.66 (m, 9H); 7.94 (s, 1H); 9.07 (br s, 1H); 9.98 (s, 1H); 10.81 (br s, 1H). HPLC analysis on Symmetry C18 column: impurities <1% (column size 3.9×150 mm; mobile phase acetonitrile −0.1 M phosphate buffer (pH 2.5), 40:60; detector UV 254 nm; flow rate 1.0 ml/min; sample concentration 0.5 mg/ml). Anal. Calcd for C19H20N2O3, %: C, 70.35; H, 6.21; N, 8.64. Found, %: C, 70.21; H, 6.20; N, 8.61.

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate (3×25 ml)
  3. washThe organic layer was washed with saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated
  6. customthe residue was crystallized from acetonitrile affording the title compound as reddish crystals (0.122 g, 38%)

Sources & evidence

ORD record
ord-560228ed54fb41acbbb5183d91cf6903
Source dataset
uspto-grants-2011_02
Patent number
US07880020B2

Reaction notes

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