Sodium Hydroxide → 3-Ethoxyisoquinoline-4-carboxylic acid

HRID 869012Notes

Reaction equation

HRID 869012 reaction equation
[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([C:13]=1[C:14]([O:16]CC)=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2].[OH-].[Na+]>CO>[CH2:1]([O:3][C:4]1[N:5]=[CH:6][C:7]2[C:12]([C:13]=1[C:14]([OH:16])=[O:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium Hydroxide2×HCID 90414090Ethyl 3-ethoxyisoquinoline-4-carboxylate

Product 1

HCID 904135253-Ethoxyisoquinoline-4-carboxylic acidYield 65.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The title compound of Step B (492 mg, 2 mmol) dissolved in MeOH (15 mL) was added NaOH(aq) 2M (2.5 mL). The reaction mixture was stirred at 60° C. for 16 h and then NaOH(aq) 4M (2 mL) was added and the mixture was stirred at 70° C. for 4 h. MeOH was evaporated and the aqueous phase was cooled to 0° C. and acidified with the addition of HCl(aq) 6N. The solid was filtered, washed with cold water and dried to afford the title compound (285 mg, 65%). MS (ESI) mass calcd. for C12H11NO3, 217.1. m/z found 218.1 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ 13.36 (s, 1H), 9.15 (s, 1H), 8.13-8.06 (m, 1H), 7.82-7.70 (m, 2H), 7.54-7.47 (m, 1H), 4.50 (q, J=7.0 Hz, 2H), 1.35 (t, J=7.0 Hz, 3H).

Workup

  1. stirringthe mixture was stirred at 70° C. for 4 h
  2. customMeOH was evaporated
  3. temperaturethe aqueous phase was cooled to 0° C.
  4. additionacidified with the addition of HCl(aq) 6N
  5. filtrationThe solid was filtered
  6. washwashed with cold water
  7. customdried

Sources & evidence

ORD record
ord-7d8c37fa78eb429787bf2c0aceca7234
Source dataset
uspto-grants-2015_03
Patent number
US08969352B2

Reaction notes

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