Methanol → Methyl Isoquinoline-4-carboxylate

HRID 1470481Notes

Reaction equation

HRID 1470481 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=[O:12])=[CH:3][N:2]=1.[CH3:14]CN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CO>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([O:13][CH3:14])=[O:12])=[CH:3][N:2]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 459768Isoquinoline-4-carboxylic acid

Product 1

HCID 11830161Methyl Isoquinoline-4-carboxylateYield 54.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of isoquinolin-4-carboxylic acid (Intermediate-14) (1.2 g, 6.9 mmol) in CH2Cl2 (10 mL) was added, EDCI (1.3 g, 8.3 mmol), HOBt (1.12 g, 8.3 mmol), DMAP (84 mg, 0.7 mmol) and the mixture was stirred at RT for 20 min. To this, MeOH (0.33 g, 10.4 mmol) was added and the reaction mixture was further stirred at RT for overnight. It was diluted with CH2Cl2 (100 mL) and washed with water. The organic layer was separated, dried over Na2SO4, filtered and concentrated to give crude product that was purified by flash column chromatography (10% EtOAc:Hexanes) to give the desired product (700 mg, 54%) as pale yellow solid.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product that
  7. customwas purified by flash column chromatography (10% EtOAc:Hexanes)

Sources & evidence

ORD record
ord-adbc1a2304b14efdb89cd11e3e8e9b26
Source dataset
uspto-grants-2015_04
Patent number
US09006442B2

Reaction notes

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