Nitric Acid → 6-Nitrophthalide

HRID 839350Notes

Reaction equation

HRID 839350 reaction equation
[N+:1]([O-:4])(O)=[O:2].CN(C)C1C=C(N(C)C)C=CC=1[C:16]1(C2C=CC(N(C)C)=CC=2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:18](=[O:19])[O:17]1>S(=O)(=O)(O)O>[N+:1]([C:22]1[CH:21]=[C:20]2[C:25]([CH2:16][O:17][C:18]2=[O:19])=[CH:24][CH:23]=1)([O-:4])=[O:2]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 204408323-(2,4-Bis(dimethylamino)phenyl)-3-(4-(dimethylamino)phenyl)phthalide

Product 1

HCID 2235846-Nitrophthalide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

Three portions of a mixture of concentrated nitric acid (0.6 ml. each portion) and concentrated sulfuric acid (0.66 ml. each portion) were added to a mixture of 3-(2,4-bis(dimethylamino)phenyl)-3-(4-(dimethylamino)phenyl)phthalide 4.17 g.) and concentrated sulfuric acid (20 ml.) with cooling. After each addition the temperature was allowed to rise to room temperature. The resulting mixture was poured onto ice and the resulting mixture was basified, affording 3-(2,4-bis(dimethylamino)phenyl)-3-(4-(dimethylamino)phenyl)-5 or 6-nitrophthalide (I: = Y4 = (CH3)2N, Y2 = Z4 = Z7 = H, Z5 or Z6 = O2N and the other of Z5 or Z6 = H) or a mixture of both.

Workup

  1. additionAfter each addition the temperature
  2. customto rise to room temperature
  3. additionThe resulting mixture was poured onto ice

Sources & evidence

ORD record
ord-51755b0206b043b2be925abd87436858
Source dataset
uspto-grants-1978_06
Patent number
US04094877

Reaction notes

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