(S)-4-(4-Aminobenzyl)oxazolidin-2-one → (S)-4-(4-hydrazinobenzyl)-2-oxazolidinone

HRID 1470541Notes

Reaction equation

HRID 1470541 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)=[CH:4][CH:3]=1.[N:15]([O-])=O.[Na+]>Cl>[NH:1]([C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)=[CH:4][CH:3]=1)[NH2:15]

Participants

4

Reactant 2

HCID 7099156(S)-4-(4-Aminobenzyl)oxazolidin-2-oneHCID 23668193Sodium Nitrite

Product 1

HCID 9990596(S)-4-(4-hydrazinobenzyl)-2-oxazolidinone

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

In an embodiment, (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one of formula (II), which was prepared using prior art methods was treated with an aqueous solution of sodium nitrite in concentrated hydrochloric acid at −5 to 10° C. After completion of reaction based on HPLC, the resulting diazonium salt was treated with stannous chloride in hydrochloric acid at −15 to 10° C. to give (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one of formula (III).

Workup

  1. customAfter completion of reaction

Sources & evidence

ORD record
ord-e5eb426f533c4940bdeb3cb6d626c521
Source dataset
uspto-grants-2015_04
Patent number
US09006453B2

Reaction notes

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