Ammonium Hydroxide → HCID 22048459, compound

HRID 1830800Notes

Reaction equation

HRID 1830800 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([C:25]4[N:29]([CH3:30])[CH:28]=[N:27][CH:26]=4)([C:20]4[S:21][CH:22]=[CH:23][N:24]=4)[OH:19])[CH:16]=3)[N:11]=[C:10]([O:31]C)[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[NH4+].[OH-]>Cl.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]([OH:19])([C:25]4[N:29]([CH3:30])[CH:28]=[N:27][CH:26]=4)[C:20]4[S:21][CH:22]=[CH:23][N:24]=4)[CH:16]=3)[NH:11][C:10](=[O:31])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 22048483HCID 22048483, compound

Product 1

HCID 22048459HCID 22048459, compoundYield 102.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (10)(0.0065 mol) in HCl 3N (100 ml) and THF (100 ml) was stirred and refluxed for 6 hours. The mixture was poured out on ice, alkalized with a concentrated NH4OH solution and extracted with DCM. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness, yielding 3 g (>100%) of 4-(3-chlorophenyl)-6-[hydroxy(1-methyl-1H-imidazol-5-yl)-2-thiazolylmethyl]-2(1H)-quinolinone (intermediate 11).

Workup

  1. temperaturerefluxed for 6 hours
  2. additionThe mixture was poured out on ice
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated till dryness

Sources & evidence

ORD record
ord-7833612cd205497c831338692bb13967
Source dataset
uspto-grants-2006_06
Patent number
US07067531B2

Reaction notes

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