Hydrochloric Acid → HCID 69227248, compound

HRID 988275Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[C:3]=1[O:4][CH2:5][C:6]#N.[OH-:28].[Na+].Cl.[OH2:31]>C(O)C>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]2[CH:27]=[CH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[N:19]=2)[C:3]=1[O:4][CH2:5][C:6]([OH:31])=[O:28]

Participants

Conditions

Temperature: 60 °C

Procedure

{2-Methyl-6-[3-(quinolin-2-ylamino)-propoxymethyl]-phenoxy}-acetonitrile (270 mg, 0.75 mmol) is dissolved in ethanol (6 mL). 10 N NaOH (750 μL, 7.5 mmol) is added, and the contents are heated to 60° C. for 4 hrs. The reaction is cooled to r.t. 2 N HCl (3.75 mL, 7.5 mmol) is added and the pH is adjusted to ˜4-6. The contents are poured into water (150 mL) and extracted with ethyl acetate (3×75 mL). The organic fractions were pooled and washed with brine (3×100 mL), dried over MgSO4, filtered and reduced under vacuum to dryness. The crude material was pure enough to test as is to give the title compound. 1H NMR (300 MHz, CDCl3) δ 11.04 (s (broad), 1H), 7.88 (d, 1H), 7.73 (d, 1H), 7.52-7.47 (m, 2H), 7.26-7.12 (m, 3H), 7.02-6.97 (m, 1H), 6.90 (d, 1H), 4.66 (s, 2H), 4.47 (s, 2H), 3.69 (t, 2H), 3.57-3.53 (m, 2H), 2.33 (s, 3H), 2.05 (quintet, 2H). MS (ESI) 381 (M+H)+.

Workup

temperatureThe reaction is cooled to r.t
extractionextracted with ethyl acetate (3×75 mL)
washwashed with brine (3×100 mL)
dry with materialdried over MgSO4
filtrationfiltered

Sources & evidence

ORD record: ord-5b1999d060e94e3bb09b824c2c863db8
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635655B1

Reaction notes

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