Hydrochloric Acid → HCID 15229930, compound

HRID 273922Notes

Reaction equation

HRID 273922 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[CH:15]([CH2:17][C:18]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH:21]=[CH:20][CH:19]=4)[CH2:14][CH2:13][CH2:12][C:11]=3[C:10]([CH2:28][OH:29])=[N:9]2)=[CH:4][CH:3]=1.N1[CH:35]=[CH:34]C=CC=1.[OH2:36].Cl>C(Cl)Cl>[C:34]([O:29][CH2:28][C:10]1[C:11]2[CH2:12][CH2:13][CH2:14][CH:15]([CH2:17][C:18]3[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][CH:19]=3)[C:16]=2[N:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)[N:9]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 1049PyridineHCID 15230055HCID 15230055, compound

Product 1

HCID 15229930HCID 15229930, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Fluorophenyl)-7-[(1-naphthyl)methyl]-4,5,6,7-tetrahydro-1H-indazole-3-methanol (CP 366, 0.864 mmol, 0.334 g) and 0.077 mL (1.35 mmol, 0.085 g) of pyridine were dissolved in 3 mL of CH2Cl2 and cooled to 0° C. under N2Acetyl chloride (1.08 mmol, 0.107 g, 0.109 mL) was added and the solution was stirred at 0° C. for 2 h. Water and 2N aqueous HCl were added and the mixture was extracted with ether. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated to give 0.350 g (94%) of the title compound as an off-white solid. Recrystallization from EtOAc:hexanes afforded 0.084 g of analytically pure white solid, m.p. 142°-144° C.; 1H NMR (CDCl3, 300 MHz) 1.5-2.1 (complex, 4H), 2.13 (s, 3H), 2.52 (m, 1H), 2.71 (m, 1H), 2.84 (dd, 1H, J=11.1, 13.8), 3.14 (dd, 1H, J=4.1, 13.8), 3.38 (m, 1H), 5.16 (s, 2H), 7.10 (d, 2H, J=8.0), 7.2-7.5 (complex, 7H). 7.68 (d, 1H, J=8.2), 7.79 (d, 1H, J=8.0); IR (KBr) 1733, 1516, 1222 cm-1 ; MS (DCI) m/z 429 (base), 369. Anal. Calcd. for Calcd. for C27H25FN2O2 : C, 75.68; H, 5.88; N, 6.54. Found: C, 75.46; H, 5.83; N, 6.29.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ether
  3. washThe organic layer was washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3afc9a7f87bb4233bd60dba9bfd255ae
Source dataset
uspto-grants-1995_02
Patent number
US05387693

Reaction notes

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