Benzoic Acid → 3-(2,4-Bis(dimethylamino)phenyl)-3-(4-(dimethylamino)phenyl)phthalide

HRID 839340Notes

Reaction equation

C(O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][N:11]([CH3:21])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N:18]([CH3:20])[CH3:19])[CH:13]=1.[C:22]([O:25][C:26](=[O:28])[CH3:27])(=O)[CH3:23].Cl>>[CH3:19][N:18]([CH3:20])[C:14]1[CH:13]=[C:12]([N:11]([CH3:21])[CH3:10])[CH:17]=[CH:16][C:15]=1[C:22]1([C:5]2[CH:4]=[CH:3][C:2]([N:11]([CH3:12])[CH3:10])=[CH:7][CH:6]=2)[C:23]2[C:27](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:26](=[O:28])[O:25]1

Participants

Reactant 4

HCID 243Benzoic Acid

HCID 313Hydrochloric Acid

HCID 7918Acetic Anhydride

HCID 897151,3-Benzenediamine, N1,N1,N3,N3-tetramethyl-

Product 1

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

Conditions

Temperature: 95 °C

Procedure

A mixture of 2-(4-dimethylamino)benzoyl)benzoic acid (26.8 g.), N,N,N',N'-tetramethyl-m-phenylenediamine (16.4 g.) and acetic anhydride (80 g.) was heated (to 95° C.) during one hour, cooled and poured into dilute hydrochloric acid. The resulting mixture was basified. Recrystallization of the resulting solid from a mixture of toluene and hexane afforded 3-(2,4-bis(dimethylamino)phenyl)-3-(4-(dimethylamino)-phenyl)phthalide (I: X = Y4 = (CH3)2N, Y2 = Z4 = Z5 = Z6 = Z7 = H) (m.p. 190°-194° C.).

Workup

temperaturecooled
customRecrystallization of the resulting solid
additionfrom a mixture of toluene and hexane

Sources & evidence

ORD record: ord-37ce92fe7e244c93a507814d05101bdb
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04094877

Reaction notes

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