Sodium Bicarbonate → HCID 20291882, compound

HRID 1413343Notes

Reaction equation

HRID 1413343 reaction equation
Cl.[N+:2]([C:5]1[CH:22]=[CH:21][CH:20]=[C:7]2[C:8]([N:10]([C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=3)[C:11](=[O:12])[C:6]=12)=[O:9])([O-:4])=[O:3].C(=O)(O)[O-].[Na+]>O>[N+:2]([C:5]1[CH:22]=[CH:21][CH:20]=[C:7]2[C:8]([N:10]([C:13]3[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=3)[C:11](=[O:12])[C:6]=12)=[O:9])([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 20291881HCID 20291881, compound

Product 1

HCID 20291882HCID 20291882, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(3-Nitrophthalimidyl)-aniline, used in the above example, can be prepared as follows: 48.3 g (0.25 mol) of 3-nitrophthalic anhydride and 37.5 g (0.25 mol) of 4-aminoacetanilide in 500 ml of acetic acid are refluxed for 8 hours and are then cooled. The crystals which have separated out are filtered off with suction, washed with 150 ml of ethanol and dried for 24 hours at 80° C./30 mm Hg. 65 g (80% of theory) of 4-(3-nitrophthalimidyl)-acetanilide are obtained; melting point 255° C. 65 g (0.2 mol) of 4-(3-nitrophthalimidyl)-acetanilide are heated with a mixture of 400 ml of dioxan and 200 ml of concentrated hydrochloric acid for 3 hours at 90° C. and the whole is then left to stand for 24 hours at 25° C. The crystals which have separated out are filtered off with suction and washed with 100 ml of methanol. 45 g (70% of theory) of crude 4-(3-nitrophthalimidyl)-aniline hydrochloride are obtained. 45 g (0.14 mol) of this hydrochloride are mixed with 100 ml of water and 200 ml of a saturated sodium bicarbonate solution are added dropwise at 5° C. After one hour, the resulting fine precipitate is filtered off with suction, washed three times with 50 ml of water and dried for 24 hours at 25° C./1 mm Hg. 21 g (54% of theory) of 4-(3-nitrophthalimidyl)-aniline are obtained; melting point 177° C. IR spectrum (KBr): 1790 and 1725 cm-1 (CO--N--CO); 1540 and 1360 cm-1 (NO2).

Workup

  1. additionare added dropwise at 5° C
  2. filtrationthe resulting fine precipitate is filtered off with suction
  3. washwashed three times with 50 ml of water
  4. customdried for 24 hours at 25° C./1 mm Hg

Sources & evidence

ORD record
ord-96a73a352a3a46bdb6e5976299dcd011
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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