Hydrochloric Acid → (R)-ethyl 6-iodo-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate hydrochloride

HRID 2061875Notes

Reaction equation

HRID 2061875 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([CH2:13][N:14]2[C:23]3[C:18](=[CH:19][C:20]([I:24])=[CH:21][CH:22]=3)[C:17](=[O:25])[C:16]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:15]2)[CH2:9]1)=O)(C)(C)C.[ClH:31]>O1CCOCC1>[ClH:31].[CH2:29]([O:28][C:26]([C:16]1[C:17](=[O:25])[C:18]2[C:23](=[CH:22][CH:21]=[C:20]([I:24])[CH:19]=2)[N:14]([CH2:13][C@@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:15]=1)=[O:27])[CH3:30]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59416180(R)-ethyl 1-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate2×

Product 1

HCID 68473754(R)-ethyl 6-iodo-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The crude (R)-ethyl 1-((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methyl)-6-iodo-4-oxo-1,4-dihydroquinoline-3-carboxylate (Intermediate 95, ˜4.4 mmol) was dissolved in 1,4-dioxane (20 mL) and 4.0M hydrogen chloride in 1,4-dioxane (20 mL) was added. The reaction mixture was stirred at room temperature for 1 h, and the solvent was removed in vacuo. The solid was then dried in a vacuum oven at 40° C. for 18 h to give 2.3 g (quant. yield) of (R)-ethyl-6-iodo-4-oxo-1-(pyrrolidin-3-ylmethyl)-1,4-dihydroquinoline-3-carboxylate hydrochloride as a yellow solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe solid was then dried in a vacuum oven at 40° C. for 18 h

Sources & evidence

ORD record
ord-928e743f4230425ca961e4a9dfbc5cf6
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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