Hydrochloric Acid → 1-(t-Butylamino)isoquinoline-5-carboxylic acid

HRID 1051242Notes

Reaction equation

[C:1]([NH:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([O:18]C)=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[Li+].[OH-].Cl>C(OCC)(=O)C>[C:1]([NH:5][C:6]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([C:16]([OH:18])=[O:17])[C:10]=2[CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 80 °C

Procedure

Methyl 1-(t-butylamino)isoquinoline-5-carboxylate (1.6 g, 6.20 mmol) obtained in Step (5) above was stirred in a solution of tetrahydrofuran (16 mL) and distilled water (16 mL). The reaction solution was added with LiOH (0.57 g, 13.6 mmol) and stirred for about 12 hours at 80° C. The reaction mixture was cooled to room temperature and adjusted to have a pH value in a range of 1˜2 by adding 1N aqueous HCl. The reaction mixture was diluted with ethyl acetate, and washed with distilled water. The organic layer thus obtained was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to obtain the title compound (0.6 g, 40%).

Workup

distillationdistilled water (16 mL)
temperatureThe reaction mixture was cooled to room temperature
washwashed with distilled water
customThe organic layer thus obtained
dry with materialwas dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-94c92720bd264ce8b8a1801283a0d438
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09388165B2

Reaction notes

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