Water → 1-(3-methyl-1H-indazol-1-yl)Ethanone

HRID 1377506Notes

Reaction equation

HRID 1377506 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12].C(N(CC)CC)C.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:11]([N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]([CH3:1])=[N:3]1)(=[O:13])[CH3:12]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 178434273HCID 178434273, compound

Product 1

HCID 126391861-(3-methyl-1H-indazol-1-yl)EthanoneYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

3-Methyl-1H-indazole (6.157 g, 44.6 mmol) in CH2Cl2 (100 mL) was treated with acetic anhydride (22.75 g, 223 mmol), triethylamine (22.5 g, 228 mmol) and DMAP (0.54 g, 4.5 mmol). The mixture was stirred 1 h at 20° C., poured into water (100 mL) and extracted with CH2Cl2 (2×100 mL). The extracts were dried (Na2SO4), concentrated and the residue recrystallised from hexane to give the title compound (4.12 g, 66%) as a white crystalline solid; mp 70°-71° C. (from hexane); 1H NMR (360 MHz, CDCl3) δ 8.41 (d, J=8.4 Hz, 1H, indazole), 7.64 (d, J=8.4 Hz, 1H, indazole), 7.54 (t, J=8.4 Hz, 1H, indazole), 7.35 (t, J=8.4 Hz, 1H, indazole), 2.75 (s, 3H, Ac), 2.58 (s, 3H, Me); MS (CI+) m/e 175 (M+H+); Anal. calcd for C10H10N2O: C, 68.95; H, 5.97; N, 16.08. Found: C, 68.80; H, 5.58; N, 16.18.

Workup

  1. extractionextracted with CH2Cl2 (2×100 mL)
  2. dry with materialThe extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. customthe residue recrystallised from hexane

Sources & evidence

ORD record
ord-fd84c784ab3542eba5eccd5c2dcf2827
Source dataset
uspto-grants-1997_09
Patent number
US05665732

Reaction notes

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