Sodium Bicarbonate → 1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-3-amine

HRID 1946349Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:6]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[N:10]2)[CH:7]=1.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[C:6]([CH2:8][N:9]2[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]2)[CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

1-({5-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-3-nitro-1H-pyrazole (for a preparation see Intermediate 54)(159 mg, 0.46 mmol) was dissolved in ethanol (10 ml). Stannous chloride (hydrated) (522 mg, 2.31 mmol) was added and the reaction was stirred and heated to 85° C. overnight under nitrogen. The reaction mixture was treated with saturated aqueous sodium bicarbonate solution. The mixture was partitioned between water and ethyl acetate. The mixture was filtered to remove the solid tin residues. The ethyl acetate layer was separated, and the aqueous layer was extracted with further ethyl acetate (2×50 ml). The combined organic fractions were concentrated in vacuo to give the title compound as an off-white solid (156 mg);

Workup

customThe mixture was partitioned between water and ethyl acetate
filtrationThe mixture was filtered
customto remove the solid tin residues
customThe ethyl acetate layer was separated
extractionthe aqueous layer was extracted with further ethyl acetate (2×50 ml)
concentrationThe combined organic fractions were concentrated in vacuo

Sources & evidence

ORD record: ord-7e41d751bbf24cb1bd68753da6e53fe0
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399436B2

Reaction notes

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