Ammonium Chloride → Methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoate

HRID 384749Notes

Reaction equation

HRID 384749 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:19][CH3:20])=[CH:8][C:9]([N+:16]([O-])=O)=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12].[Cl-].[NH4+]>O.CO.[Fe]>[NH2:16][C:9]1[CH:8]=[C:7]([O:19][CH3:20])[C:6]([O:5][CH2:4][CH2:3][CH2:2][Cl:1])=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 11666631Methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate

Product 1

HCID 23032997Methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoateYield 93%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Med. Chem., 44, 3965 (2001) describes a process for preparing a 4-alkoxy-5-halogenoalkoxyanthranilic acid compound from a 4-alkoxy-5-halogenoalkoxy-2-nitrobenzoic acid compound. For example, methyl 5-(3-chloropropoxy)-4-methoxy-2-nitrobenzoate is reacted with a very excessive amount of iron and ammonium chloride in a mixture of water and methanol, to give methyl 2-amino-5-(3-chloropropoxy)-4-methoxybenzoate (i.e., methyl 5-(3-chloropropoxy)-4-methoxyanthranilate) in 93% yield.

Sources & evidence

ORD record
ord-0b1a04cda16e47e998d843d7a284c2da
Source dataset
uspto-grants-2013_02
Patent number
US08367824B2

Reaction notes

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