N,N-Dimethylaniline → 5-Aminosalicylic Acid

HRID 1762883Notes

Reaction equation

HRID 1762883 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:5](=[CH:7][CH:8]=[C:9]([NH2:11])[CH:10]=1)[OH:6].CN(C)C1C=CC=CC=1.[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](Cl)=[O:29]>>[Br:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([NH:11][C:9]1[CH:8]=[CH:7][C:5]([OH:6])=[C:4]([CH:10]=1)[C:3]([O:2][CH3:1])=[O:12])=[O:29].[NH2:11][C:9]1[CH:10]=[C:4]([C:3]([OH:12])=[O:2])[C:5]([OH:6])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 898486-Bromohexanoyl chlorideHCID 135127Methyl 5-amino-2-hydroxybenzoate

Product 2

HCID 40755-Aminosalicylic AcidHCID 14500512HCID 14500512, compound

Procedure

was prepared in quantitative yield from 40.0 g (0.24 mol) of methyl-5-aminosalicylate, 32.0 g (0.26 mol) of N,N-dimethylaniline and 46.5 g (0.22 mol) of 6-bromohexanoyl chloride according to the procedure of Example 9, part a. The methyl 5-aminosalicylate was obtained by Fischer esterification of 5-aminosalicylic acid. The product was not recrystallized, but was obtained directly from trituration in 1N HCl, mp 100°-102° C.

Sources & evidence

ORD record
ord-f0265e364c0c4b719109b8ad763fa598
Source dataset
uspto-grants-1989_05
Patent number
US04835180

Reaction notes

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