7-Chloromethyl-1,4-dichloro-isoquinoline → 4-chloro-7-(hydroxymethyl)-1(2H)-isoquinolone

HRID 2289820Notes

Reaction equation

HRID 2289820 reaction equation
ClCC1C=C2C(C(Cl)=CN=C2Cl)=CC=1.[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([C:26](OCC)=[O:27])=[CH:23][CH:24]=2)[C:19](=[O:31])[NH:18][CH:17]=1>C1COCC1>[Cl:15][C:16]1[C:25]2[C:20](=[CH:21][C:22]([CH2:26][OH:27])=[CH:23][CH:24]=2)[C:19](=[O:31])[NH:18][CH:17]=1

Participants

4

Reactant 2

HCID 186983127-Chloromethyl-1,4-dichloro-isoquinolineHCID 18698325Ethyl 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinecarboxylate

Product 1

HCID 186984304-chloro-7-(hydroxymethyl)-1(2H)-isoquinoloneYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

7-(Chloromethyl)-1,4-dichloro-isoquinoline ##STR186## LiBH4 (530 mg, 24.3 mmol) was added portionwise to a stirred solution of ethyl 4-chloro-1-oxo-1,2-dihydro-7-isoquinolinecarboxylate (3.06 g, 12.2 mmol) in THF (100 mL) and the mixture was stirred at room temperature for 1 h. The heterogeneous mixture was quenched with dilute HCl (2 M), and extracted with CH2Cl7 (2×100 mL) and EtOAc (5×100 mL). The remaining solid was taken up in hot EtOH, and allowed to cool to yield a white fluffy solid. This solid was combined with the combined organic extracts, evaporated in vacuo and crystallised with EtOH to give 4-chloro-7-(hydroxymethyl)-1(2H)-isoquinolone (2.19 g, 10.49 mmol) as a white solid.

Workup

  1. customThe heterogeneous mixture was quenched with dilute HCl (2 M)
  2. extractionextracted with CH2Cl7 (2×100 mL) and EtOAc (5×100 mL)
  3. temperatureto cool
  4. customto yield a white fluffy solid
  5. customevaporated in vacuo
  6. customcrystallised with EtOH

Sources & evidence

ORD record
ord-8f71c2a4eb4345d680effc9fd3c5fda7
Source dataset
uspto-grants-2000_07
Patent number
US06093731

Reaction notes

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