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

HRID 987171Notes

Reaction equation

HRID 987171 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-1c17ce149584488da34e311784c996eb
Source dataset
uspto-grants-2003_10
Patent number
US06630577B2

Reaction notes

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