Hydrazine hydrate (1:1) → 5-Benzyloxy-6-methoxy-2H-phthalazin-1-one

HRID 2268878Notes

Reaction equation

HRID 2268878 reaction equation
O.[NH2:2]N.[CH2:4]([O:11][C:12]1[C:13]([CH:27]=O)=[C:14]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[C:15]([N:17](CC)CC)=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(O)(=O)C>[CH2:4]([O:11][C:12]1[C:24]([O:25][CH3:26])=[CH:23][CH:22]=[C:14]2[C:13]=1[CH:27]=[N:2][NH:17][C:15]2=[O:16])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 185047883-benzyloxy-N,N-diethyl-2-formyl-4-methoxy-benzamide

Product 1

HCID 183746425-Benzyloxy-6-methoxy-2H-phthalazin-1-oneYield 96%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Glacial acetic acid (285 ml) at 10-20° C. was dropwise added with hydrazine monohydrate (10.16 ml, 209 mmoles) and added with 3-benzyloxy-N,N-diethyl-2-formyl-4-methoxy-benzamide (14.27 g, 41.8 mmoles), prepared as described in example 56. The mixture was left to stand for 2 hours, then evaporated, dissolved in CH2Cl2, washed with water, anhydrified over Na2SO4, brought to dryness, and the crude was triturated in petrolatum/ethyl ether 2:1 (150 ml) and filtered to give 11.3 g of the title compound (yield: 96%).

Workup

  1. customprepared
  2. waitThe mixture was left
  3. customevaporated
  4. dissolutiondissolved in CH2Cl2
  5. washwashed with water
  6. customthe crude was triturated in petrolatum/ethyl ether 2:1 (150 ml)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-796d27652c63437a918f70eaff8f2295
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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