Hydrochloric Acid → HCID 54747354, compound

HRID 2046260Notes

Reaction equation

HRID 2046260 reaction equation
[CH3:1][C:2]([C:5]1[C:6]([OH:17])=[C:7]([C:12]([O:14]CC)=O)[C:8](=[O:11])[NH:9][N:10]=1)([CH3:4])[CH3:3].[CH3:18][C:19]([O-])([CH3:21])[CH3:20].[K+].[ClH:24].[OH2:25]>>[Cl:24][C:18]1[CH:3]=[CH:2][CH:1]=[CH:20][C:19]=1[CH2:21][N:9]1[C:8](=[O:11])[C:7]([C:12]([NH:10][CH2:5][C:6]([OH:17])=[O:25])=[O:14])=[C:6]([OH:17])[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])=[N:10]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 23665647Potassium tert-butoxideHCID 68812135HCID 68812135, compound

Product 1

HCID 54747354HCID 54747354, compoundYield 69%

Conditions

Temperature
150 °C

Procedure

Ethyl 6-(1,1-dimethylethyl)-5-hydroxy-3-oxo-2,3-dihydro-4-pyridazinecarboxylate. KOtBu (1M solution in t-BuOH, 9.4 mL, 9.38 mmol) was added to the compound from example 45b) (1.79 g, 6.25 mmol). The reaction was heated in the microwave at 150° C. for 20 minutes. The reaction was cooled and H2O was added followed by 1N HCl to precipitate the product. The solid was filtered to give the title compound (1.04 g, 69%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.73 (s, 1H) 12.64 (s, 1H) 4.30 (q, J=7.07 Hz, 2H) 1.30 (s, 9H) 1.28 (t, J=7.20 Hz, 3H).

Workup

  1. temperatureThe reaction was cooled
  2. customto precipitate the product
  3. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-21c002b6efb54ea6bf85c630f3033ebe
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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