Nitric Acid → 6-Nitrophthalide

HRID 839544Notes

Reaction equation

HRID 839544 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: X = 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. temperaturewith cooling
  2. additionAfter each addition the temperature
  3. customto rise to room temperature
  4. additionThe resulting mixture was poured onto ice

Sources & evidence

ORD record
ord-eada3cba17e94dfe80c0dfd6de17f2b0
Source dataset
uspto-grants-1978_06
Patent number
US04096176

Reaction notes

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