Sodium Hydroxide → 1-(4-Methoxybenzylamino)isoquinoline-7-carboxylic acid

HRID 880968Notes

Reaction equation

HRID 880968 reaction equation
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([O:21]CC)=[O:20])[CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([C:19]([OH:21])=[O:20])[CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67491573Ethyl 1-(4-methoxybenzylamino)isoquinoline-7-carboxylate

Product 1

HCID 674916931-(4-Methoxybenzylamino)isoquinoline-7-carboxylic acidYield 83.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 1-(4-methoxybenzylamino)isoquinoline-7-carboxylate (430 mg, 1.28 mmol) in methanol (8.5 mL) was added 6 N aqueous sodium hydroxide (1.1 mL, 6.4 mmol). The reaction was stirred at room temperature overnight. The reaction was concentrated. The residue was taken up in water and acidified with 1 N aqueous hydrochloric acid until a precipitate formed. The solid was collected by filtration and dried under vacuum to give the title compound (328 mg, 83%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6, δ): 8.92 (s, 1H), 8.30 (t, J=5.8 Hz, 1H), 8.06 (dd, J=8.4, 1.4Hz, 1H), 7.88 (d, J=5.7 Hz, 1H), 7.69 (d, J=8.6 Hz, 1H), 7.24-7.31 (m, 2H), 6.88 (d, J=5.7 Hz, 1H), 6.79-6.85 (m, 2H), 4.62 (d, J=5.9 Hz, 2H), 3.67 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated
  2. customformed
  3. filtrationThe solid was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cc2fbba415ac432abf4d66194079e72d
Source dataset
uspto-grants-2015_03
Patent number
US08993586B2

Reaction notes

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