Hydrochloric Acid → N-[4-(Hydroxymethyl)-2-nitrophenyl]acetamide

HRID 262525

反応式

HRID 262525 の反応式
ClC(OC)=O.[C:6]([NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=1[N+:19]([O-:21])=[O:20])(=[O:8])[CH3:7].[BH4-].[Na+].Cl>O1CCCC1.O.C(OCC)(=O)C.C(N(CC)CC)C>[OH:15][CH2:14][C:13]1[CH:17]=[CH:18][C:10]([NH:9][C:6](=[O:8])[CH3:7])=[C:11]([N+:19]([O-:21])=[O:20])[CH:12]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 737584-Acetamido-3-nitrobenzoic acidHCID 4311764Sodium borohydride

生成物 1

HCID 13196334N-[4-(Hydroxymethyl)-2-nitrophenyl]acetamide収率 40.5%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

8.3 ml (108 mmol) methyl chloroformate dissolved in 25 ml tetrahydrofuran (THF) is added dropwise over 15 minutes to a solution of 23.9 g (107 mmol) 4-(acetylamino)-3-nitrobenzoic acid and 14.8 ml (107 mmol) triethylamine in 150 ml dry THF under nitrogen and chilled in an acetone/ice bath. The temperature is kept below -5°. After stirring at -5° for 30 minutes, the triethylamine.HCl is filtered off and washed with 30 ml cold THF. The combined filtrates are added dropwise to a stirred solution of 10.3 g (108 mmol) sodium borohydride in 100 ml water chilled in an acetone/ice bath. The temperature is not allowed to exceed 15°. The resulting mixture is stirred at room temperature for 4 hours. After acidification with concentrated hydrochloric acid, the reaction mixture is taken up in ethyl acetate which is washed with water, 10% NaOH (X 2), water (X 2), dried (Na2SO 4), and evaporated: 17 g. This material is crystallized from 20 ml methanol to give 9.1 g of the title compound, m.p. 114°-115°.

後処理

  1. temperaturechilled in an acetone/ice bath
  2. customis kept below -5°
  3. filtrationHCl is filtered off
  4. washwashed with 30 ml cold THF
  5. temperaturechilled in an acetone/ice bath
  6. customto exceed 15°
  7. stirringThe resulting mixture is stirred at room temperature for 4 hours
  8. washis washed with water, 10% NaOH (X 2), water (X 2)
  9. dry with materialdried (Na2SO 4)
  10. customevaporated
  11. customThis material is crystallized from 20 ml methanol

出典と根拠

ORDレコード
ord-e21663fe45154cc28b3e3674cd69a861
出典データセット
uspto-grants-1979_05
特許番号
US04154846

関連ノート

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