Hydrochloric Acid → HCID 89812860, compound

HRID 1480942Notes

Reaction equation

HRID 1480942 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7](Br)[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].O.CCOC(C)=O.Cl.[CH3:32][N:33]1CCCC1=O>>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([C:32]#[N:33])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 89813003Methyl 1-bromo-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Product 1

HCID 89812860HCID 89812860, compoundYield 70%

Conditions

Temperature
130 °C

Procedure

To a mixture of 1-bromo-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (2.0 g, 5.34 mmol) in 16.2 mL of N-methylpyrrolidone was heated in a 130° C. oil bath for 2 h. After cooled, the reaction mixture was poured into a mixture of 100 mL of water (containing 5% conc. NH4OH) and EtOAc (100 mL). It was vigorously stirred at room temperature for 30 min, then was acidified by conc. HCl solution until two phases became clear. Organic layer was washed with water, brine and dried over MgSO4. It was filtered and concentrated. Crude product was triturated with MeOH and white solid was collected to provide the title compound 1.20 g (3.75 mmol) in 70% yield. LC-MS ESI+: 321.31 (M+1)+.

Workup

  1. temperatureAfter cooled
  2. washOrganic layer was washed with water, brine
  3. dry with materialdried over MgSO4
  4. filtrationIt was filtered
  5. concentrationconcentrated
  6. customCrude product was triturated with MeOH and white solid
  7. customwas collected

Sources & evidence

ORD record
ord-8d982f50483b43a69888246f7cfd6603
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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