Water → HCID 11608549, compound

HRID 1831614Notes

Reaction equation

HRID 1831614 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]2[O:10][CH2:11][O:12][C:7]2=[CH:6][C:3]=1[C:4]#N.[CH2:13]([Mg]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.[OH:23]S(O)(=O)=O>C1COCC1.CCOCC>[NH2:1][C:2]1[CH:9]=[C:8]2[O:10][CH2:11][O:12][C:7]2=[CH:6][C:3]=1[C:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:23]

Participants

7

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 6879796-Amino-1,3-benzodioxole-5-carbonitrileHCID 178418336HCID 178418336, compound

Product 1

HCID 11608549HCID 11608549, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 1.5 g (10.0 mmol) of 2-amino-4,5-methylenedioxy-benzonitrile in THF (40 mL) was added CuBr (50 mg, 0.34 mmol) and benzylmagnesium chloride (40 mL, 1.0 M solution in Et2O). The reaction mixture was refluxed for 12 h. After cooling to 25° C., H2O (5 mL) was added followed by 15% H2SO4 (15 mL). After stirring for 14 h, ether (50 mL) was added. Organic layer was separated. Aqueous layer was extracted with ether (2×50 mL). The combined organic layer was dried and evaporated. Following chromatography (silica gel, CHCl3), 1.2 g (52%) of the title compound was obtained. IR (CHCl3) 1675 cm−1 MS m/z 255 (M+).

Workup

  1. temperatureThe reaction mixture was refluxed for 12 h
  2. customOrganic layer was separated
  3. extractionAqueous layer was extracted with ether (2×50 mL)
  4. customThe combined organic layer was dried
  5. customevaporated

Sources & evidence

ORD record
ord-9aab117bfd1c4b4ca14b13dc01775781
Source dataset
uspto-grants-2006_06
Patent number
US07067666B2

Reaction notes

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