Ammonia → 7-Bromo-1-Chloroisoquinoline

HRID 549266Notes

Reaction equation

HRID 549266 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][N:13]=[C:14]2O)=[CH:9][CH:8]=1.N>>[Br:6][C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][N:13]=[C:14]2[Cl:3])=[CH:9][CH:8]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 178517616HCID 178517616, compound

Product 1

HCID 65020247-Bromo-1-ChloroisoquinolineYield 115%

Conditions

Temperature
100 °C

Procedure

To phosphorus oxychloride (46.6 mL, 0.5 mol) at room temperature was added, portionwise, 7-bromo-1-hydroxyisoquinoline (11.2 g, 0.05 mol). The mixture was heated to 100° C. for 90 min with rapid stirring. On cooling to room temperature, the mixture was poured, cautiously onto ice/water (200 mL). Dropwise addition of aqueous ammonia raised the pH=8 and the resulting precipitate was collected by filtration, washing with cold water. The solid was dried under reduced vacuum at 45° C. for 12 h. 13.86 g (115%) Beige solid isolated. 1H NMR (DMSO-d6) δ 8.4 (s, 1H), 8.34-8.38 (d, J=6 Hz, 1H), 8.03-8.07 (m, 2H), 7.91-7.96 (d, J=6 Hz, 1H); HPLC: 96%; LCMS: 242, 244, 246.

Workup

  1. temperatureOn cooling to room temperature
  2. additionthe mixture was poured, cautiously onto ice/water (200 mL)
  3. temperatureraised the pH=8
  4. filtrationthe resulting precipitate was collected by filtration
  5. washwashing with cold water
  6. customThe solid was dried under reduced vacuum at 45° C. for 12 h

Sources & evidence

ORD record
ord-132c87bf729841acbeae36cdab8ee2b1
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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