Triethylamine → HCID 136156458, compound

HRID 1362913Notes

Reaction equation

HRID 1362913 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[O:9][CH:8]=[C:7]([C:15]1[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=1)[C:6]2=[O:25])[CH3:2].Cl.NO.C([N:31](CC)CC)C>CCO.O>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[C:7]1[CH:8]=[N:31][O:25][C:6]=1[C:5]1[CH:4]=[C:3]([CH2:1][CH3:2])[C:12]([O:13][CH3:14])=[CH:11][C:10]=1[OH:9]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 58712199HCID 58712199, compound

Product 1

HCID 136156458HCID 136156458, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-ethyl-7-methoxy-3-naphthalen-2-yl-chromen-4-one (e, 0.36 g), hydroxylamine hydrochloride (0.6 g), triethylamine (0.5 mL) in EtOH (10 mL) was heated at 140° C. in microwave reactor for 4 h. The mixture was diluted with water (100 mL) and extracted with CH2Cl2 (2×50 mL). The combined organic extracts were washed with water and dried using a drying agent. The oil obtained on concentration was flash chromatograghed on silica gel to give 4-(naphthalen-2-yl)-5-(2-hydroxy-4-methoxy-5-ethyl-phenyl) isoxazole as white powder (f, 0.19 g). 1H-NMR (CDCl3) δ (ppm) 8.57 (s, 1H), 7.8 (m, 4H), 7.5 (m, 3H), 7.10 (s, 1H), 6.52 (s, 2H), 3.92 (s, 3H), 2.4 (q, 2H, J=7), 1.0 (t, 3H, J=7); ESMS clcd for C22H19NO3: 345.1; Found: 346.0 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (2×50 mL)
  2. washThe combined organic extracts were washed with water
  3. customdried
  4. customThe oil obtained on concentration

Sources & evidence

ORD record
ord-d4675d118309494f9b597cd51fc9c1fb
Source dataset
uspto-grants-2011_02
Patent number
US07884094B2

Reaction notes

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