Triethylamine → 3-Chloro-benzofuro[3,2-c]isoquinoline-5-ol

HRID 869425Notes

Reaction equation

HRID 869425 reaction equation
COC(=O)[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[C:13](OC)=[O:14])Br.[OH:18][C:19]1[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=1[C:21]#[N:22].C(N(CC)CC)C>CC#N>[Cl:12][C:9]1[CH:8]=[C:7]2[C:6]([C:4]3[O:18][C:19]4[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=4[C:21]=3[N:22]=[C:13]2[OH:14])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 119072-HydroxybenzonitrileHCID 867222712-(4-Chloro-2-methoxycarbonyl-phenyl)-2-bromo-acetic acid methyl ester

Product 1

HCID 1785169623-Chloro-benzofuro[3,2-c]isoquinoline-5-olYield 56.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 19A (crude, 20.29 mmol) and 2-hydroxy-benzonitrile (20.29 mmol) in MeCN (100 mL) was stirred at room temperature. To the solution was added triethylamine (TEA, 20.44 g, 202.9 mmol) dropwise. After addition completed, the reaction was refluxed for 24 hours, then cooled. The precipitated solids were collected by filtration, washed with a small amount of MeCN, then washed with water several times until there was no TEA salt, dried to give pure product 19B (3.1 g).

Workup

  1. additionAfter addition
  2. temperaturethe reaction was refluxed for 24 hours
  3. temperaturecooled
  4. filtrationThe precipitated solids were collected by filtration
  5. washwashed with a small amount of MeCN
  6. washwashed with water several times until there
  7. customdried

Sources & evidence

ORD record
ord-e40dfa1c9ea24f92b74a4bff7a070602
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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