Hydrochloric Acid → 3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-amine

HRID 1466553Notes

Reaction equation

HRID 1466553 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[C:12]([NH:13]C(=O)OC(C)(C)C)=[CH:11][N:10]([CH3:21])[N:9]=2)[CH:7]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH3:23])=[C:6]([C:8]2[C:12]([NH2:13])=[CH:11][N:10]([CH3:21])[N:9]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66847419HCID 66847419, compound

Product 1

HCID 668510103-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirring solution of tert-butyl 3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-ylcarbamate (543.2 mg, 1.608 mmol, 1 eq) was added hydrogen chloride (5.0 mL of a 4.0 M solution in 1,4-dioxane, 0.020 mol, 12 eq). The reaction mixture was stirred at room temperature for 9 hours and then evaporated to dryness. The solid residue was partitioned between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous portion was extracted once more with dichloromethane, and the combined organic extracts dried over magnesium sulfate and concentrated to give 3-(5-chloro-2-methoxyphenyl)-1-methyl-1H-pyrazol-4-amine, which was carried forward without purification. LCMS (ESI) m+H=238.2; 1H NMR (400 MHz, CDCl3) δ: 7.53 (s, 1H), 7.28 (d, 1H), 7.02 (s, 1H), 6.91 (d, 1H), 3.91 (d, 2H), 3.87 (s, 3H), 3.84 (s, 3H).

Workup

  1. customevaporated to dryness
  2. customThe solid residue was partitioned between dichloromethane
  3. extractionThe aqueous portion was extracted once more with dichloromethane
  4. dry with materialthe combined organic extracts dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8f01f199fe414711aaa09a8e6d8a448a
Source dataset
uspto-grants-2015_04
Patent number
US08999998B2

Reaction notes

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