Hydrochloric Acid → HCID 14989659, compound

HRID 1199686Notes

Reaction equation

HRID 1199686 reaction equation
N([O-])=O.[Na+].N[C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:10][CH:11]=1.[S:19](=[O:21])=[O:20].[ClH:22]>O.C(O)(=O)C>[Cl:22][S:19]([C:6]1[CH:7]=[CH:8][C:9]([CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[N:10][CH:11]=1)(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 14989647HCID 14989647, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 14989659HCID 14989659, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Conditions

Temperature
-10 °C

Procedure

Sodium nitrite (6.08 g) in water (12 ml) was added over 20 minutes to a solution of methyl 4-(5-aminopyrid-2-yl)butanoate (7.48 g, 0.04 mole) in glacial acetic acid (20 ml) and concentrated hydrochloric acid (32 ml) stirred at -10° C. The solution was stirred for 15 minutes then added over 15 minutes to a solution of cuprous chloride (2 g) in glacial acetic acid saturated with sulphur dioxide at 10° C. The resulting solution was stirred at room temperature for 1 hour then poured into ice water (250 ml) and extracted with chloroform (3×200 ml). The chloroform extracts were dried over magnesium sulphate and the solvent was removed to give the title compound as a pale green oil which was used without further purification.

Workup

  1. stirringThe solution was stirred for 15 minutes
  2. stirringThe resulting solution was stirred at room temperature for 1 hour
  3. extractionextracted with chloroform (3×200 ml)
  4. dry with materialThe chloroform extracts were dried over magnesium sulphate
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-d8fa763cdec24de4bb89bc53b5ff7985
Source dataset
uspto-grants-1990_02
Patent number
US04902698

Reaction notes

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