2H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo- → 1,3-dioxo-2-isoindolineacetic acid, [[N-[2-(o-chlorobenzoyl)-4-nitrophenyl]-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide

HRID 1076616Notes

Reaction equation

HRID 1076616 reaction equation
[NH2:1][N:2]1[C:11]([OH:19])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:18])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:20]([O-:22])=[O:21])[CH:9]=2)[N:4]=[CH:3]1.[C:23]1(=[O:37])[N:27]([CH2:28][C:29](Cl)=[O:30])[C:26](=[O:32])[C:25]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:24]12>N1C=CC=CC=1>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]([C:10]1[CH:9]=[C:8]([N+:20]([O-:22])=[O:21])[CH:7]=[CH:6][C:5]=1[N:4]([CH:3]=[N:2][NH:1][C:29](=[O:30])[CH2:28][N:27]1[C:23](=[O:37])[C:24]2[C:25](=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:26]1=[O:32])[C:29](=[O:30])[CH2:28][N:27]1[C:26](=[O:32])[C:25]2[C:24](=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:23]1=[O:37])=[O:19]

Participants

4

Reactant 2

HCID 812422H-Isoindole-2-acetyl chloride, 1,3-dihydro-1,3-dioxo-HCID 215373033-Amino-6-nitro-3,4-dihydro-4-hydroxy-4-(o-chlorophenyl)quinazoline

Product 1

HCID 1317102371,3-dioxo-2-isoindolineacetic acid, [[N-[2-(o-chlorobenzoyl)-4-nitrophenyl]-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In the manner given in Example 1, 3-amino-6-nitro-3,4-dihydro-4-hydroxy-4-(o-chlorophenyl)quinazoline with pyridine is reacted with α-phthalimidoacetyl chloride to give 1,3-dioxo-2-isoindolineacetic acid, [[N-[2-(o-chlorobenzoyl)-4-nitrophenyl]-1,3-dioxo-2-isoindolineacetamido]methylene]hydrazide.

Sources & evidence

ORD record
ord-a7f2ad6807fe4d55b66aa1c5f957bb63
Source dataset
uspto-grants-1976_05
Patent number
US03957761

Reaction notes

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