Ethanol → Dianiline

HRID 1975793Notes

Reaction equation

HRID 1975793 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](CC(O)=O)=[CH:4][C:3]=1[N+:12]([O-])=O.[CH2:15]([OH:17])[CH3:16]>[Pd]>[CH:5]1[CH:4]=[C:3]([NH2:12])[C:2]([NH:1][C:15]([C:16]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)=[O:17])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 15052973HCID 15052973, compound

Product 1

HCID 42725Dianiline

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

4-Amino-3-nitrophenylacetic acid (0.97 g) and the product from Example 15 (1.0 g) were treated by the procedure described in Example 19. The intermediate product was hydrogenated over palladium in ethanol to yield the intermediate dianiline. Treatment of this intermediate with 2,3-dihydroxy-1,4-dioxane, followed by conversion to the methanesulfonate addition salt yielded 0.88 g. of the desired product. m.p. 192° C. 1H NMR (DMSO-d6, 300 MHz) δ1.7-2.0 (m, 4H), 2.3 (s, 3H), 2.4-3.6 (m, 9H), 3.03 (d, 3H), 3.79 (s, 3H), 6.84 (d, 1H), 6.90 (d, 1H), 7.16 (t, 1H), 7.85 (dd, 1H), 8.1 (m, 2H), 8.96 (m, 2H), 9.1 (bs, 1H). Anal calcd for C24H31N3O4S: C, 62.99; H, 6.83; N, 9.18. Found: C, 62.79; H, 6.96; N, 9.00.

Sources & evidence

ORD record
ord-51bbdecdddb24bd9a55748822459ca7a
Source dataset
uspto-grants-1994_02
Patent number
US05288749

Reaction notes

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