Hydrochloric Acid → HCID 136082911, compound

HRID 1788000Notes

Reaction equation

HRID 1788000 reaction equation
C[O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:8][NH:9]2)=[CH:5][CH:4]=1.Cl.N1C=CC=CC=1.Cl>C(OCC)(=O)C>[OH:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])=[N:8][NH:9]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10176127Pyridinium chlorideHCID 66749847HCID 66749847, compound

Product 1

HCID 136082911HCID 136082911, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 24.2 g (82.5 mmol) of 2-({6-methoxy}-1H-indazol-3-yl)-1H-isoindole-1,3(2H)-dione and 73.4 g (0.635 mol) of piridine hydrochloride was heated at 200° C. for 4 hours. The resulting brown solution was cooled to 140° C. and slowly poured in a well stirred mixture of 250 ml of 0.2 N HCl and 350 ml of ethyl acetate. The organic layer was separated and the aqueous layer was salted (45 g of NaCl) and extracted twice with 350 ml of ethyl acetate. Organic extracts were dried over sodium sulfate and concentrated under vacuum to small volume. The precipitate was filtered off and dried: 15.89 g of product as yellow solid were obtained. Yield=68.9%. mp=265-270° C. dec.

Workup

  1. temperatureThe resulting brown solution was cooled to 140° C.
  2. additionslowly poured in a well
  3. customThe organic layer was separated
  4. extractionextracted twice with 350 ml of ethyl acetate
  5. dry with materialOrganic extracts were dried over sodium sulfate
  6. concentrationconcentrated under vacuum to small volume
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-f12aead606f24a7b964da767f75a6aec
Source dataset
uspto-grants-2009_03
Patent number
US07511136B2

Reaction notes

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