Sodium Dithionite → HCID 19094232, compound

HRID 487184Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]1[C:18]([N+:19]([O-])=O)=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([OH:14])=[O:13].S(S([O-])=O)([O-])=O.[Na+].[Na+]>>[NH2:19][C:18]1[C:10]([NH:9][CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([OH:14])=[O:13]

Participants

Reactant 2

HCID 24489Sodium Dithionite

HCID 19094224HCID 19094224, compound

Product 1

HCID 19094232HCID 19094232, compoundYield 85%

Procedure

2-[(2-chlorophenyl)methyl]amino-3-nitrobenzoic acid (22 g, 72 mmol) was reduced with sodium hydrosulfite by the method described in Example 2(ii) to provide 3-amino-2-[(2-chlorophenyl)methyl]aminobenzoic acid in 85% yield; mp 203°-204° C. This amine was acylated with excess valeryl chloride in the presence of excess 10% sodium hydroxide solution and toluene. The resulting valeryl derivative was heated in acetic acid and hydrochloric acid according to the procedure described in Method A to provide the title compound.

Sources & evidence

ORD record: ord-cb8e7a12cf2f4a46895de76be14896b4
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05294631

Reaction notes

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