Methyl 2-methyl-1,3-dioxolane-2-butanoate → 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[4-(2-methyl-1,3-dioxolan-2-yl)-1-oxobutyl]hydrazide

HRID 1646898

Reaction equation

HRID 1646898 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=O)[O:6][CH2:5][CH2:4][O:3]1.[Cl:14][C:15]1[CH:33]=[CH:32][C:18]2[O:19][C:20]3[CH:31]=[CH:30][CH:29]=[CH:28][C:21]=3[CH2:22][N:23]([C:24]([NH:26][NH2:27])=[O:25])[C:17]=2[CH:16]=1>>[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][C:10]([NH:27][NH:26][C:24]([N:23]2[CH2:22][C:21]3[CH:28]=[CH:29][CH:30]=[CH:31][C:20]=3[O:19][C:18]3[CH:32]=[CH:33][C:15]([Cl:14])=[CH:16][C:17]2=3)=[O:25])=[O:12])[O:3][CH2:4][CH2:5][O:6]1

Participants

3

Reactant 2

HCID 3310317Methyl 2-methyl-1,3-dioxolane-2-butanoateHCID 135604618-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide

Product 1

HCID 867465088-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[4-(2-methyl-1,3-dioxolan-2-yl)-1-oxobutyl]hydrazide

Procedure

8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, 2-[4-(2-methyl-1,3-dioxolan-2-yl)-1-oxobutyl]hydrazide (26) was prepared in the manner described above in Example 18 from methyl 2-methyl-1,3-dioxolane-2-butanoate (25), prepared as described above in Example 25, and 8-chlorodibenz[b,f][1,4]oxazepine-10(11H)-carboxylic acid, hydrazide (1), prepared in the manner described above in Example 1, on a 2 mmol scale to yield 0.47 g (53%) of product. Analysis calculated for C22H24N3O5Cl 0.2 H2O (M.W. 449.51): C, 58.79; H, 5.74; N, 9.35; Cl, 9.15. Found: C, 58.47; H, 5.58; N, 9.30; Cl, 9.15.

Workup

  1. customprepared
  2. customprepared in the manner

Sources & evidence

ORD record
ord-f331246721be4fc19d0596e171131bf6
Source dataset
uspto-grants-1993_01
Patent number
US05182272

Linked notes

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