Acetic Acid → HCID 66713284, compound

HRID 523785Notes

Reaction equation

HRID 523785 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][NH:5][C:6]([C:8]1[C:9](=[O:23])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7].[N-]=[N+]=[N-].[Na+].[NH3:29].[C:30]([OH:33])(=O)[CH3:31]>OS(O)(=O)=O>[CH3:1][O:2][C:3](=[O:24])[CH2:4][NH:5][C:6]([C:8]1[N:29]=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:15]2[C:10]([C:9]=1[O:23][C:30](=[O:33])[CH3:31])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 33557Sodium AzideHCID 66713131HCID 66713131, compound

Product 1

HCID 66713284HCID 66713284, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

[(1-Oxo-3-phenyl-1H-indene-2-carbonyl)-amino]-acetic acid methyl ester (1.864 g, 5.8 mmol) was dissolved in a mixture of concentrated H2SO4 (16 ml) and glacial acetic acid (16 ml) at 50 to 60° C. Then NaN3 (985 mg, 15 mmol) was added in portions with stirring so that the temperature did not exceed 60° C. Stirring was then continued at 50 to 60° C. for additional 30 min before the mixture was poured onto ice (200 g). The resulting mixture was basified by addition of concentrated aqueous NH3 (55 ml, D=0.89 g/ml) and extracted with CH2Cl2 (2×100 ml). The combined organic phases were dried over MgSO4 and then filtered through silica gel. The filtrate was discarded. The silica gel was washed with EtOAc (ca. 400 ml). The resulting solution was concentrated in vacuo to give a dark oil (250 mg). Further purification by flash column chromatography on silica gel using EtOAc and then EtOAc:hexanes=7:3 as the eluent gave the title compound as a tan solid (19 mg); 1H NMR (CDCl3): δ=7.11 to 7.98 (m), 3.75 (d, 2H), 3.68 (s, 1H), 2.19 (s, 3H).

Workup

  1. customdid not exceed 60° C
  2. stirringStirring
  3. additionwas poured onto ice (200 g)
  4. extractionextracted with CH2Cl2 (2×100 ml)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered through silica gel
  7. washThe silica gel was washed with EtOAc (ca. 400 ml)
  8. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-8e36c6309e6a48f2b5d34d8426f89abd
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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