Pyridine → alpha-Cyano-6-bromo-2,3-dimethoxycinnamic acid

HRID 2290917ノート

反応式

HRID 2290917 の反応式
[Br:1][C:2]1[C:7]([CH:8]=O)=[C:6]([O:10][CH3:11])[C:5]([O:12][CH3:13])=[CH:4][CH:3]=1.[C:14]([CH2:16][C:17]([OH:19])=[O:18])#[N:15].N1C=CC=CC=1>C1C=CC=CC=1>[C:14]([C:16](=[CH:8][C:7]1[C:2]([Br:1])=[CH:3][CH:4]=[C:5]([O:12][CH3:13])[C:6]=1[O:10][CH3:11])[C:17]([OH:19])=[O:18])#[N:15]

参加物

5

反応物 3

HCID 1049PyridineHCID 9740Cyanoacetic acidHCID 46719526-Bromo-2,3-dimethoxybenzaldehyde

生成物 1

HCID 53869906alpha-Cyano-6-bromo-2,3-dimethoxycinnamic acid収率 71.8%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A mixture of 6-bromo-2,3-dimethoxybenzaldehyde (48.4 g, 0.20 mole), NH4OAc (1.93 g, 0.025 mole), cyanoacetic acid (0.186 mole, 15.8 g), pyridine (42 mL), and benzene (193 mL) was stirred at reflux for 2 hours using a Dean-Stark trap for water removal. Upon cooling to room temperature a solid was filtered and washed with hexane. The solid was dissolved in 1N KOH, and was extracted with ether. The aqueous layer was acidified with 10% HCl and was extracted with CH2Cl2. The combined CH2Cl2 layers were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield 41.7 g yellow solid, (67%); mp 130°-2°; M+ 311.

後処理

  1. temperatureat reflux for 2 hours
  2. customfor water removal
  3. filtrationwas filtered
  4. washwashed with hexane
  5. dissolutionThe solid was dissolved in 1N KOH
  6. extractionwas extracted with ether
  7. extractionwas extracted with CH2Cl2
  8. washThe combined CH2Cl2 layers were washed with water, saturated aqueous NaCl
  9. dry with materialdried (MgSO4)
  10. filtrationfiltered
  11. customevaporated

出典と根拠

ORDレコード
ord-dde66f44ec154ac1af74ffbea120cdc5
出典データセット
uspto-grants-1986_10
特許番号
US04618683

反応ノート

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