2-Bromobenzaldehyde → HCID 68786075, compound

HRID 2097959Notes

Reaction equation

HRID 2097959 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[CH3:10][O:11][CH:12]([O:15][CH3:16])[CH2:13][NH2:14]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[N:14]=[CH:13][CH:12]([O:15][CH3:16])[O:11][CH3:10]

Participants

4

Reactant 2

HCID 811292-BromobenzaldehydeHCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 68786075HCID 68786075, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-bromobenzaldehyde (18.4 g, 0.1 mol) and 2,2-dimethoxyethanamine (11.55 g, 0.11 mol) in 200 mL of toluene was heated to reflux for 4 hr. The reaction mixture was evaporated under vacuum to give an oil of 2-bromo-N-(2,2-dimethyoxyethylidene)aniline which was used for the next step without purification. The oil was dropped into 50 mL of concentrated H2SO4 and the mixture was heated to 130-140° C. for 30 mins, then the reaction mixture was poured into 500 mL if ice-water and adjust to pH˜8 with 5N sodium hydroxide solution. The aqueous solution was extracted with DCM (250 mLX5) and washed with water (3×50 mL). The combined organic layer was washed with brine, dried over Na2SO4 and the solvent was evaporated under vacuum. The crude solid was purified with silica gel to give 8-bromoisoquinoline (2.2 g, two steps 10.6%).

Workup

  1. temperatureto reflux for 4 hr
  2. customThe reaction mixture was evaporated under vacuum

Sources & evidence

ORD record
ord-74d50f5a75e442289b0f4d957d638128
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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