3-Bromoaniline → HCID 19379668, compound

HRID 2209964Notes

Reaction equation

HRID 2209964 reaction equation
C([CH:4]1[C:9](=O)[CH2:8][C:7](=[O:11])[O:6][C:5]1=[O:12])(=O)C.[Br:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17]>C(O)(=O)C>[Br:13][C:14]1[CH:15]=[C:16]2[C:18]([C:9]([CH2:4][C:5]([OH:12])=[O:6])=[CH:8][C:7](=[O:11])[NH:17]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 19379709HCID 19379709, compound

Product 1

HCID 19379668HCID 19379668, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a suspension of 3-acetyl-tetrahydropyran-2,4,6-trione (25 g, 0.147 mol) and acetic acid (50 ml) was added a solution of m-bromoaniline (25.3 g, 0.147 mol) in acetic acid (30 ml) at room temperature. The reaction was continuted under the same conditions for 30 minutes. The reaction mixture was poured into ice-water (1 L) and then the separated solid was filtered off by aspiration. The residue was washed with water and dried. The obtained solid (54 g) was added in small portions to concentrated sulfuric acid (250 ml) and stirred at room temperature for 16 hours. The reaction mixture was poured into ice-water and then the separated solid was filtered off by aspiration. The residue was washed with methanol and acetone and then dried to give 7-bromo-l,2-dihydro-2-oxo-4-quinolineacetic acid (19.5 g) as a white solid. The solid (19.5 g) was suspended in methanol 500 ml. Thionyl chloride 15.1 ml (207 mmol) was added dropwise thereto at room temperature and the mixture was refluxed for 0.5 hour. The reaction mixture was poured into ice-water (1 L) and then the separated solid was filtered off by aspiration. The residue was washed with water and recrystallized from methanol to give the entitled compound as white crystals (mp 208°-210 ° C. (from methanol), 13.6 g, yield 31.2 %).

Workup

  1. filtrationthe separated solid was filtered off by aspiration
  2. washThe residue was washed with water
  3. customdried
  4. additionThe obtained solid (54 g) was added in small portions to concentrated sulfuric acid (250 ml)
  5. additionThe reaction mixture was poured into ice-water
  6. filtrationthe separated solid was filtered off by aspiration
  7. washThe residue was washed with methanol and acetone
  8. customdried

Sources & evidence

ORD record
ord-baa1eb917cb84ecc887cfdac5e2abff1
Source dataset
uspto-grants-1995_10
Patent number
US05457099

Reaction notes

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