Ethanol → Ethyl 1-chloroisoquinoline-7-carboxylate

HRID 880966Notes

Reaction equation

HRID 880966 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12](Cl)=[O:13])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.C([OH:17])C.C(N([CH2:23][CH3:24])CC)C>O1CCCC1>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:13][CH2:23][CH3:24])=[O:17])[CH:10]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 874207001-Chloroisoquinoline-7-carbonyl chloride

Product 1

HCID 86664617Ethyl 1-chloroisoquinoline-7-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

1-Chloroisoquinoline-7-carbonyl chloride (3.02 g, 13.4 mmol) was dissolved in tetrahydrofuran (135 mL) and was cooled to 0° C. Ethanol (6.1 mL, 94 mmol) and triethylamine (2.05 mL, 14.7 mmol) were added. The reaction was allowed to warm to room temperature and stir for 2 hours. The reaction mixture was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (250 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to give the title compound (3.0 g, 96%) as a yellow solid. +ESI (M+H) 236.1; 1H NMR (400 MHz, CDCl3, δ): 9.06 (s, 1H), 8.30-8.39 (m, 2H), 7.89 (d, J=8.6 Hz, 1H), 7.63 (d, J=5.7 Hz, 1H), 4.48 (q, J=7.1 Hz, 2H), 1.46 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction mixture was partitioned between ethyl acetate (500 mL) and saturated aqueous sodium bicarbonate (250 mL)
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fac4407511e84e1d8e5a7f3d1d8c50cb
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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