Hydrochloric Acid → 6-(5-Amino-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochloride

HRID 1774723Notes

Reaction equation

HRID 1774723 reaction equation
CC(C)(C)C([NH:5][C:6]1[CH:7]=[N:8][CH:9]=[C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17](=[O:23])[CH2:16][CH2:15]3)[CH:11]=1)=O.[ClH:26]>>[ClH:26].[NH2:5][C:6]1[CH:11]=[C:10]([C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]([CH3:22])[C:17](=[O:23])[CH2:16][CH2:15]3)[CH:9]=[N:8][CH:7]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 866791042,2-Dimethyl-N-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yl]-propionamide

Product 1

HCID 866791056-(5-Amino-pyridin-3-yl)-1-methyl-3,4-dihydro-1H-quinolin-2-one hydrochlorideYield 69%

Conditions

Temperature
90 °C

Procedure

A suspension of 2,2-dimethyl-N-[5-(1-methyl-2-oxo-1,2,3,4-tetrahydro-quinolin-6-yl)-pyridin-3-yl]-propionamide (0.195 g, 0.578 mmol) in 1N aqueous HCl (5.78 mL) was heated to 90° C. over night. The reaction mixture was evaporated to dryness and the resulting solid material was triturated in MeOH, filtered off and further dried in a the high vacuum to give the title compound (0.115 g, 69%) as an off white solid as the HCl salt. MS: 254.1 (M+H+).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe resulting solid material was triturated in MeOH
  3. filtrationfiltered off
  4. customfurther dried in a the high vacuum

Sources & evidence

ORD record
ord-2e5a8430b1d4407987e5d4f7dbf78d00
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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