Acetic Acid → HCID 57875744, compound

HRID 536557Notes

Reaction equation

HRID 536557 reaction equation
[Cl: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]([Cl: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 124815-Chloro-salicylaldehydeHCID 70091tert-Butyl carbazateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 57875744HCID 57875744, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-chloro-2-hydroxybenzaldehyde (1.5 g, 9.3 mmol), tert-butylcarbazate (1.25 g, 9.3 mmol) and acetic acid (0.54 mL, 9.3 mmol) in CH2Cl2 (50 mL) was stirred under a N2 atmosphere for 30 min at RT. Then sodium triacetoxyborohydride (6.20 g, 27.9 mmol) was added portion wise and the resulting mixture was stirred at RT overnight. The reaction was thoroughly quenched with 2 M HCl (15 mL) and stirred at RT for 1 h. The reaction mixture was partitioned between water (50 mL) and CH2Cl2 (25 mL). The aqueous layer was extracted with CH2Cl2 (25 mL). The combined organic layers were washed with water (2×75 mL), dried (Na2SO4) and evaporated to dryness to give hydrazine 1 as a white solid, 2.6 g (100%).

Workup

  1. customThe reaction was thoroughly quenched with 2 M HCl (15 mL)
  2. stirringstirred at RT for 1 h
  3. customThe reaction mixture was partitioned between water (50 mL) and CH2Cl2 (25 mL)
  4. extractionThe aqueous layer was extracted with CH2Cl2 (25 mL)
  5. washThe combined organic layers were washed with water (2×75 mL)
  6. dry with materialdried (Na2SO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0ee8f50fe83b4de29c355f1db69ceed9
Source dataset
uspto-grants-2014_10
Patent number
US08859606B2

Reaction notes

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