Ethanol → Ethyl 7-bromoisoquinoline-3-carboxylate

HRID 1245058Notes

Reaction equation

HRID 1245058 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=O)[C:5]([CH:8]=O)=[CH:6][CH:7]=1.C(O[N:19]([CH2:22][CH3:23])CC)(=O)CC([O-])=O.[O-:24][CH2:25][CH3:26].[Na+].C([OH:30])C>>[CH2:25]([O:24][C:23]([C:22]1[N:19]=[CH:10][C:4]2[C:5]([CH:8]=1)=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[O:30])[CH3:26]

Participants

5

Reactant 4

HCID 702EthanolHCID 2723922Sodium ethoxideHCID 132552574-Bromobenzene-1,2-dicarbaldehydeHCID 86592791HCID 86592791, compound

Product 1

HCID 69083434Ethyl 7-bromoisoquinoline-3-carboxylateYield 78%

Procedure

A mixture of 4-bromo-benzene-1,2-dicarbaldehyde (0.450 g, 2.137 mmol), diethylamino malonate (0.452 g, 2.137 mmol), and sodium ethoxide (0.218 g, 3.20 mmol) in anhydrous ethanol (15 mL) was refluxed for 4 hr. The solution was cooled to rt and concentrated under reduced pressure. The crude residue was purified by flash column chromatography (silica gel, 0.5% MeOH in CHCl3) to obtain 0.460 g (78%) of the 7-bromo-isoquinoline-3-carboxylic acid ethyl ester which was hydrolyzed according to general procedure C yielding the 0.350 g (85%) of 7-bromo-isoquinoline-3-carboxylic acid as a white solid. LC/MS (m/z): 253 (M+1)+.

Workup

  1. temperaturewas refluxed for 4 hr
  2. concentrationconcentrated under reduced pressure
  3. customThe crude residue was purified by flash column chromatography (silica gel, 0.5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-38b03af3006b4d4ab672cf9980649715
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

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