N1,N3-bis(1,3-dihydroxypropan-2-yl)-5-nitroisophthalamide → 5-amino-N,N'-bis[2-hydroxy-1-(hydroxymethyl)ethyl]-1,3-benzenedicarboxamide

HRID 1048832Notes

Reaction equation

[OH:1][CH2:2][CH:3]([NH:6][C:7](=[O:25])[C:8]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[C:10]([C:11]([NH:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])=[O:12])[CH:9]=1)[CH2:4][OH:5]>O.[Ni]>[NH2:22][C:20]1[CH:21]=[C:8]([C:7]([NH:6][CH:3]([CH2:4][OH:5])[CH2:2][OH:1])=[O:25])[CH:9]=[C:10]([CH:19]=1)[C:11]([NH:13][CH:14]([CH2:17][OH:18])[CH2:15][OH:16])=[O:12]

Participants

Conditions

Temperature: 90 °C

Procedure

N,N′-Bis-(2-hydroxy-1-hydroxymethyl-ethyl)-5-nitro-isophthalamide (40 g) is dissolved in water (600 mL), and then heated to 90° C. to dissolve. Raney Ni (5 g) is added, and allowed to react for 10 h under a H2 pressure of 1.5 MPa. Raney Ni is removed by filtration and the filter cake washed with 20-30 mL of water. The filtrate and washings are combined to obtain the aqueous solution of 5-Amino-N,N′-bis-(2-hydroxy-1-hydroxymethyl-ethyl)-isophthalamide, which can be utilized directly in the iodination reaction or concentrated and then re-crystallized using methanol to obtain solid product.

Workup

dissolutionto dissolve
customto react for 10 h under a H2 pressure of 1.5 MPa
customRaney Ni is removed by filtration
washthe filter cake washed with 20-30 mL of water

Sources & evidence

ORD record: ord-5a719f71aa6b4c34b1eedeb810fc70f5
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382194B2

Reaction notes

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