HCID 21312554, compound → HCID 21312553, compound

HRID 971899Notes

Reaction equation

HRID 971899 reaction equation
[C:1]([CH:4]1[NH:9][CH2:8][C:7]2[S:10][CH:11]=[CH:12][C:6]=2[CH:5]1[OH:13])([OH:3])=[O:2].[N:14]([O-])=[O:15].[Na+]>Cl>[C:1]([CH:4]1[N:9]([N:14]=[O:15])[CH2:8][C:7]2[S:10][CH:11]=[CH:12][C:6]=2[CH:5]1[OH:13])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 21312554HCID 21312554, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 21312553HCID 21312553, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
10 °C

Procedure

To a magnetically stirred suspension of 20 g (0.1 mole) 5-carboxy-4-hydroxy-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine in 200 cc 3 N hydrochloric acid maintained at 10° C. is added dropwise a 10% aqueous sodium nitrite solution (200 cc; 2.9 equivalents) and the resulting mixture is stirred at room temperature for 3 hours. The reaction medium remains heterogeneous throughout this step and nitrous fumes are evolved. The resulting precipitate is filtered off, washed with water and dried in vacuo, to give beige crystals (paste melting from 100° C.) in a yield of 21.3 g (93%).

Workup

  1. filtrationThe resulting precipitate is filtered off
  2. washwashed with water
  3. customdried in vacuo
  4. customto give beige crystals (paste melting from 100° C.) in a yield of 21.3 g (93%)

Sources & evidence

ORD record
ord-b45e9b45dc85400ca7b76b314b888705
Source dataset
uspto-grants-1979_07
Patent number
US04161599

Reaction notes

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