Acetic Acid → HCID 57875744, compound

HRID 453321Notes

Reaction equation

HRID 453321 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-ae8a23716c394a5e8d2cd3298bbf6cd6
Source dataset
uspto-grants-2013_07
Patent number
US08492424B2

Reaction notes

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