Acetic Acid → HCID 57875608, compound

HRID 575930Notes

Reaction equation

HRID 575930 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=O.[C:11]([O:15][C:16](=[O:19])[NH:17][NH2:18])([CH3:14])([CH3:13])[CH3:12].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:11]([O:15][C:16]([NH:17][NH:18][CH2:7][C:6]1[CH:9]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[OH:10])=[O:19])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 70091tert-Butyl carbazateHCID 728635-BromosalicylaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57875608HCID 57875608, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-bromo-2-hydroxybenzaldehyde (10 g g 50 mmol), tert-butylcarbazate (6.7 g, 52 mmol) and acetic acid (3 mL, 52 mmol) in CH2Cl2 (200 mL) was stirred under N2 atmosphere for 60 min at RT. Then sodium triacetoxyborohydride (34 g, 159 mmol) was added portion wise and the resulting mixture was stirred at RT overnight. The reaction was quenched with 2 M HCl (100 mL) and stirred at RT for 1 h. The reaction mixture was partitioned between water (100 mL) and CH2Cl2 (250 mL). The organic layer was washed with sat. NaHCO3 and brine (100 mL each), dried (MgSO4) and evaporated to dryness to give hydrazine 1 as a white solid, 13 g (82%).

Workup

  1. customThe reaction was quenched with 2 M HCl (100 mL)
  2. stirringstirred at RT for 1 h
  3. customThe reaction mixture was partitioned between water (100 mL) and CH2Cl2 (250 mL)
  4. washThe organic layer was washed with sat. NaHCO3 and brine (100 mL each)
  5. dry with materialdried (MgSO4)
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-545292e06af7453b9990665695771074
Source dataset
uspto-grants-2015_05
Patent number
US09035071B2

Reaction notes

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