Hydrochloric Acid → 3-Amino-3,4-dihydro-1,5-naphthyridin-2(1h)-one dihydrochloride

HRID 1178447Notes

Reaction equation

HRID 1178447 reaction equation
[Cl:1]C1SC2[NH:6][C:7]([C:9]([NH:11][CH:12]3[CH2:21][C:20]4[C:15](=CC=CC=4)[N:14](CCOC)[C:13]3=O)=[O:10])=[CH:8]C=2C=1.[ClH:28]>C(Cl)Cl.O1CCOCC1>[ClH:1].[ClH:28].[NH2:6][CH:7]1[CH2:8][C:13]2[C:12](=[CH:21][CH:20]=[CH:15][N:14]=2)[NH:11][C:9]1=[O:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 102506062-Chloro-N-{1-[2-(methoxy)ethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

Product 1

HCID 219068583-Amino-3,4-dihydro-1,5-naphthyridin-2(1h)-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl (2-oxo-1,2,3,4-tetrahydro-1,5-naphthyridine-3-yl)carbamate (Method 26, 263 mg, 1 mmol) was dissolved in DCM (10 mL) and treated with 4M HCl in dioxan (10 mL). After stirring at ambient temperature for 30 mins. the reaction mixture was evaporated under reduced pressure and the residue triturated with ether (20 mL), to give a white solid which was collected by filtration, washed with ether and dried. (234 mg, 100%).

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customthe residue triturated with ether (20 mL)
  3. customto give a white solid which
  4. filtrationwas collected by filtration
  5. washwashed with ether
  6. customdried

Sources & evidence

ORD record
ord-f143c4c28ca54a0dba4b9dc85fe9bcc9
Source dataset
uspto-grants-2007_10
Patent number
US07276517B2

Reaction notes

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