Glyoxylic Acid → Hydrazine hydrate (1:1)

HRID 498236Notes

Reaction equation

HRID 498236 reaction equation
C[O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[N:12][CH:11]=2)[CH:5]=1.[C:17]([OH:21])(=[O:20])[CH:18]=[O:19].[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][CH:29]=[O:30])[CH:23]=1>C(O)CCC>[C:22]([O:21][C:17](=[O:20])[CH2:18][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[N:12][CH:11]=2)[CH:5]=1)([CH3:31])([CH3:27])[CH3:23].[OH:30][CH:29]1[O:16][C:3](=[O:2])[CH:4]=[C:28]1[C:24]1[CH:23]=[C:22]([CH3:31])[CH:27]=[CH:26][CH:25]=1.[OH2:19].[NH2:12][NH2:13]

Participants

7

Reactant 3

HCID 760Glyoxylic AcidHCID 175272Benzeneacetaldehyde, 3-methyl-HCID 69489609Methyl 3-(pyridazin-4-yl)benzoate

Product 3

HCID 24654Hydrazine hydrate (1:1)HCID 223177085-Hydroxy-4-m-tolylfuran-2(5h)-oneHCID 694895143-Oxo-3-(3-pyridazin-4-yl-phenyl)-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

The title compound was prepared from 3-pyridazin-4-yl-benzoic acid methyl ester [prepared by the following sequence: i.) An equimolar mixture of glyoxylic acid and m-tolyl-acetaldehyde [CAS-No. 72927-80-1] was heated to 135° C. for 17 h. ii.) The obtained crude 5-hydroxy-4-(m-tolyl)-2(5H)-furanone and hydrazine hydrate in BuOH were refluxed for 18 h according to J. Med. Chem. 1987, 30, 239. iii.) The obtained 5-m-tolyl-2H-pyridazin-3-one was heated with excess phosphorous oxychloride to 95° C. for 4 h. iv.) The obtained 3-chloro-5-m-tolyl-pyridazine was hydrogenated in MeOH and EtOAc over 5% Pd/C in the presence of NaOAc at 23° C. v.) The obtained 4-m-tolyl-pyridazine was oxidized with KMnO4 in aqueous HOAc at 100° C. for 4 h. vi.) The obtained 3-pyridazin-4-yl-benzoic acid was esterified with SOCl2 in MeOH at 60° C.] by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a yellow oil (554 mg).

Workup

  1. customprepared by the following sequence

Sources & evidence

ORD record
ord-83b1e1dad60843598c228058efa81817
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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