Sulfuric Acid → methyl N-(3,4-dibromobenzoyl)-6-aminohexanoate

HRID 987171ノート

反応式

HRID 987171 の反応式
OS(O)(=O)=O.[Br:6][C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=1[Br:24])[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[O:11].[C:25]([O-])(O)=O.[Na+]>CO>[Br:6][C:7]1[CH:8]=[C:9]([CH:21]=[CH:22][C:23]=1[Br:24])[C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20][CH3:25])=[O:19])=[O:11]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 22988601N-(3,4-dibromobenzoyl)-6-aminohexanoic acid

生成物 1

HCID 22988604methyl N-(3,4-dibromobenzoyl)-6-aminohexanoate収率 96%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

Added conc. H2SO4 (0.2 mL) to a solution of N-(3,4-dibromobenzoyl)-6-aminohexanoic acid (1.73 g, 4.4 mmol) in methanol (50 mL). Heated under reflux for 2 hours until reaction complete (as determined by TLC). Allowed solution to cool to room temperature and neutralized by adding NaHCO3 solution. Removed solvent in vacuo and extracted residue with ether (2×50 mL). Washed extract with brine (2×30 mL) and dried over anhydrous MgSO4. Filtered extract and dried filtrate under high vacuum to afford a white solid. Obtained 1.72 g (96% yield) of methyl N-(3,4-dibromobenzoyl)-6-aminohexanoate. 1H NMR (300 MHz, DMSO-d6): δ8.59 (triplet, J=5.7 Hz, 1H), 8.16 (doublet, J=1.8 Hz, 1H), 7.84 (doublet, J=8.1 Hz, 1H), 7.73 (doublet of doublets, J=8.1, 1.8 Hz, 1H), 3.55 (singlet, 3H), 3.21 (doublet of triplets, J=6.0, 6.6 Hz, 2H), 2.28 (triplet J=7.3 Hz, 2H), 1.51 (multiplet, 4H), 1.28 (multiplet, 2H). 13C NMR (300 MHz, DMSO-d6): δ173.55, 164.05, 135.67, 133.96, 132.31, 128.20, 127.09, 124.13, 51.19, 39.20, 33.21, 28.56, 25.89, 24.15.

後処理

  1. temperatureHeated
  2. temperatureunder reflux for 2 hours until reaction complete (as determined by TLC)
  3. extractionRemoved solvent in vacuo and extracted residue with ether (2×50 mL)
  4. washWashed
  5. extractionextract with brine (2×30 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationFiltered
  8. extractionextract
  9. customdried filtrate under high vacuum to afford a white solid

出典と根拠

ORDレコード
ord-1c17ce149584488da34e311784c996eb
出典データセット
uspto-grants-2003_10
特許番号
US06630577B2

反応ノート

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