Hydrochloric Acid → HCID 28399932, compound

HRID 423305Notes

Reaction equation

HRID 423305 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([O:15]CC)=[O:14])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1.[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:13]([OH:15])=[O:14])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59318347HCID 59318347, compound

Product 1

HCID 28399932HCID 28399932, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 5-chloro-6-(1-pyrrolidinyl)-3-pyridinecarboxylate (D14) (1.06 g, 4.16 mmol) in ethanol (20 mL) and aqueous sodium hydroxide (2M, 2.08 mL, 4.16 mmol) was heated at 40° C. for 18 h. The reaction mixture was allowed to cool and was neutralised with 2M HCl (aq.). The title compound formed as a white solid and was filtered off and washed with methanol to give the title compound (243 mg, 1.08 mmol) SJ108923-113A3. The filtrate was trapped on an SCX column, eluting with 2M ammonia in methanol to give further title compound as an orange solid (467 mg, 2.07 mmol). δH (methanol-d4, 400 MHz): 8.55 (1H, d), 8.03 (1H, d), 3.76-3.70 (4H, m), 1.96-1.90 (4H, m). MS (ES): C10H11ClN2O2 requires 226, 228; found 227, 229 (MH+).

Workup

  1. temperatureto cool

Sources & evidence

ORD record
ord-a5d10345d69f4ad89bc714176a35d6c9
Source dataset
uspto-grants-2012_01
Patent number
US08101775B2

Reaction notes

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