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Methanol → Methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylate

HRID 1524306
Notes
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Reaction equation

HRID 1524306 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.C(N(CC)CC)C.CN([CH:23]=[O:24])C.[CH3:25][OH:26]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:25][O:26][C:23]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2)=[O:24]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 42609191Methyl 1-oxo-1,2-dihydroisoquinoline-6-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst

Conditions

Temperature
70 °C

Procedure

To a mixture of 6-bromo-2H-isoquinolin-1-one (4.00 g, 17.9 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (750 mg, 0.92 mmol), triethylamine (9.0 mL, 65 mmol) in a Parr bomb add a 1:1 mixture (v/v) of DMF and MeOH. Seal the apparatus and flush with 100 psi of carbon monoxide (3×). Heat the reaction mixture at 70° C. with stifling for 15 h. Remove the solvent in vacuo and wash the residue with MeOH then crystallize from dichloromethane to give 3.11 g of the desired product 1-oxo-1,2-dihydro-isoquinoline-6-carboxylic acid methyl ester as an off white solid in 86% yield.

Workup

  1. customSeal the apparatus
  2. customflush with 100 psi of carbon monoxide (3×)
  3. customRemove the solvent in vacuo
  4. washwash the residue with MeOH
  5. customthen crystallize from dichloromethane

Sources & evidence

ORD record
ord-06bb70c7aa344f0bb48e5658da529e1b
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09079880B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes