Hydrochloric Acid → 3-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile, dihydrochloride

HRID 2234245Notes

Reaction equation

HRID 2234245 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]#[N:19])[CH:15]=2)[NH:10][CH2:9]1)(C)(C)C.[ClH:21].O1CCOCC1>C(Cl)Cl>[ClH:21].[ClH:21].[NH2:7][CH:8]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:18]#[N:19])[CH:15]=2)[NH:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66692977tert-Butyl (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)carbamate

Product 1

HCID 1317281063-Amino-1,2,3,4-tetrahydroquinoline-6-carbonitrile, dihydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-cyano-1,2,3,4-tetrahydroquinolin-3-yl)-carbamic acid tert-butyl ester (546 mg, 2 mmol), prepared as described in Example 1C, in CH2Cl2 (5 mL) at 0° C. was added 4 M HCl in dioxane (4 mL, 16 mmol). After addition, the reaction mixture was stirred at RT for 2 h, then concentrated. The residue was stripped with ether (3×), and the resulting off-white solid dried in vacuo to afford the title compound (490 mg, 100%).

Workup

  1. additionAfter addition
  2. concentrationconcentrated
  3. customthe resulting off-white solid dried in vacuo

Sources & evidence

ORD record
ord-ec68a6b5bc94422984ba29e7b6119f66
Source dataset
uspto-grants-2010_05
Patent number
US07709647B2

Reaction notes

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