Ethanol → Ethyl 3-ethoxyisoquinoline-4-carboxylate

HRID 2175937Notes

Reaction equation

HRID 2175937 reaction equation
[OH:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.[C:17]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:18]=1.C(O)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[CH2:17]([O:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 178470073HCID 178470073, compound

Product 1

HCID 90414090Ethyl 3-ethoxyisoquinoline-4-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the title compound of Step A (583 mg, 2.68 mmol) in THF (13 mL) was added triphenylphosphine (1.06 g, 4.03 mmol), ethanol (0.24 mL, 4.03 mmol) and DIAD (0.79 mL, 4.03 mmol). The reaction mixture was stirred at room temperature for 16 h and then the solvent was evaporated. The crude was purified via silica gel chromatography (0-30% EtOAc in hexanes) to afford the title compound of Step B (498 mg, 76%). MS (ESI) mass calcd. for C14H15NO3, 245.1; m/z found 246.1 [M+H]+. 1H NMR (500 MHz, Chloroform-d) δ 8.97 (s, 1H), 7.91-7.82 (m, 2H), 7.65-7.60 (m, 1H), 7.42-7.36 (m, 1H), 4.59-4.48 (m, 4H), 1.48-1.39 (m, 6H).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified via silica gel chromatography (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d3283112797046c4b2d2e8cbf681572e
Source dataset
uspto-grants-2015_06
Patent number
US09062078B2

Reaction notes

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