Sodium Dithionite → HCID 18315463, compound

HRID 487181Notes

Reaction equation

HRID 487181 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[CH:11]=[C:12]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[C:13]([OH:15])=[O:14].C(=O)(O)[O-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>O1CCCC1>[NH2:19][C:18]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=1[NH:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 24489Sodium Dithionite2×HCID 516892Sodium Bicarbonate2×HCID 53829316HCID 53829316, compound

Product 1

HCID 18315463HCID 18315463, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-[(2-chlorophenyl)methyl]amino-4-nitrobenzoic acid (6 g, 19.6 mmol), tetrahydrofuran (60 mL) and 5% sodium bicarbonate solution (50 mL) was treated portionwise with sodium hydrosulfite (4 g). The resulting clear solution had a pH of 6.29 that was adjusted to pH 7.15 by the addition of solid sodium bicarbonate. Additional sodium hydrosulfite was added (12 g) over several hours, and the mixture was stirred overnight. The tetrahydrofuran phase was separated, concentrated and triturated with ether/methylene chloride/hexane to afford 5.07 g of solid. Crystallization from methanol followed by washing with cold dilute aqueous methanol provided 4.79 g (88%) of pink-to-white crystals of 4-amino-3-[(2-chlorophenyl)methyl]aminobenzoic acid; mp 176°-177° C.

Workup

  1. customThe tetrahydrofuran phase was separated
  2. concentrationconcentrated
  3. customtriturated with ether/methylene chloride/hexane

Sources & evidence

ORD record
ord-98738b20a502418185ad1ab95112c3bb
Source dataset
uspto-grants-1994_03
Patent number
US05294631

Reaction notes

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