Water → HCID 178474346, compound

HRID 1295452Notes

Reaction equation

HRID 1295452 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([OH:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:13])[CH:8]=2)[N:3]=1.[C:14](OC(=O)C)(=[O:16])[CH3:15].S(=O)(=O)(O)O.O>C(O)(=O)C>[Br:13][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([NH:1][C:14](=[O:16])[CH3:15])[CH:11]=[C:10]2[OH:12]

Participants

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 7918Acetic AnhydrideHCID 178507923HCID 178507923, compound

Product 1

HCID 178474346HCID 178474346, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2-amino-6-bromo-quinolin-4-ol (29.4 g, 0.12 mol), acetic anhydride (36.7 g, 0.36 mol) and sulphuric acid (20 ml) in glacial acetic acid (300 ml) was refluxed for 30 min. The mixture was allowed to cool to rt and then poured into water. The precipitate was isolated by filtration and dried to afford product N-(6-bromo-4-hydroxy-quinolin-2-yl)-acetamide as a brown solid (32 g, 93%). This material was used in the next step without further purification.

Workup

  1. temperaturewas refluxed for 30 min
  2. customThe precipitate was isolated by filtration
  3. customdried

Sources & evidence

ORD record
ord-def4fbe4c3194d1cbc1b2a962be9abc8
Source dataset
uspto-grants-2007_07
Patent number
US07241893B2

Reaction notes

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