Hydrochloric Acid → HCID 68517707, compound

HRID 1948351Notes

Reaction equation

HRID 1948351 reaction equation
[Cl:1][C:2]1[C:6]([CH3:7])=[C:5]([Cl:8])[NH:4][C:3]=1[C:9]([O:11]CC)=[O:10].C(O)C.O.Cl>O>[Cl:1][C:2]1[C:6]([CH3:7])=[C:5]([Cl:8])[NH:4][C:3]=1[C:9]([OH:11])=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19096565Water ethanolHCID 68515648HCID 68515648, compound2×

Product 1

HCID 68517707HCID 68517707, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.1 gm (4.95 mmol) of ethyl 3,5-dichloro-4-methyl-1H-pyrrole-2-carboxylate (Intermediate 194) and 1.7 g (9.9 mmol) of Ba(OH)2 in 50 ml 1:1 EtOH—H2O was heated at 85° C. for 9 h. The mixture was diluted with water, acidified with 20 ml 1N HCl and extracted 3 times with ether. The ether was washed with water, dried (MgSO4) and concentrated to give 1.0 g of product as a solid. MS (ES) (M−H−): 194 for C6H5Cl2NO2; NMR (d6-DMSO): 1.9 (s, 3H), 12.7 (s, 1H), 12.8 (s, 1H).

Workup

  1. extractionextracted 3 times with ether
  2. washThe ether was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f4dd22118cdb4a1e8627743a9a9d8f7f
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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