Sodium Nitrite → Hydrochloric Acid

HRID 59345Notes

Reaction equation

HRID 59345 reaction equation
[NH2:1][C:2]1[C:3]([F:17])=[C:4]([CH:13]=[CH:14][C:15]=1[Cl:16])[CH2:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9].[N:18]([O-])=O.[Na+]>O>[ClH:16].[Cl:16][C:15]1[CH:14]=[CH:13][C:4]([CH2:5][NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH3:9])=[C:3]([F:17])[C:2]=1[NH:1][NH2:18]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 56839978N-(3-amino-4-chloro-2-fluorobenzyl)pivalamide

Product 2

HCID 313Hydrochloric AcidHCID 90018790N-(4-chloro-2-fluoro-3-hydrazinylbenzyl)pivalamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The title compound was prepared according to the procedure described in step-2 of Intermediate-7 by using N-(3-amino-4-chloro-2-fluorobenzyl)pivalamide (0.500 g, 1.93 mmol), sodium nitrite (0.200 g, 2.90 mmol), stannous chloride. H2O (4.84 g, 1.09 mmol), conc. HCl (20.0 g) and water (3 mL) to afford 0.300 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 1.12 (s, 9H), 4.23 (d, J=5.4 Hz, 2H), 4.34 (br s, 2H), 5.91 (s, 1H), 6.65 (t, J=7.8 Hz, 1H), 8.02 (m, 1H); MS (m/z): 274.08 (M+H+).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-f3337546a00d4ca1901ff371760c0f28
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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