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Sodium Hydroxide → 2-Amino-1,2,3,4-tetrahydro-1,4-phthalazinedione sodium salt

HRID 41962
Notes
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Reaction equation

HRID 41962 reaction equation
O.O.[Na:3].[NH2:4][N:5]1[NH:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:16].[N+](C1C=CC=C2C(OC(=O)C=12)=O)([O-])=O.O.NN.[N+](C1(C(O)=O)C=CC=CC1C(NN)=O)([O-])=O.NC1C=CC=C(C(NN)=O)C=1C(NN)=O.NC1(C(NN)=O)C=CC=CC1C(NN)=O.BrBr.[OH-].[Na+]>[Al].[Ni]>[Na:3].[NH2:4][N:5]1[NH:14][C:13](=[O:15])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 8

HCID 14798Sodium HydroxideHCID 216313-Nitrophthalic anhydrideHCID 24408BromineHCID 24654Hydrazine hydrate (1:1)2×HCID 2455213-Aminobenzene-1,2-dicarbohydrazideHCID 668119642-Aminophthalohydrazide2×
HCID 87227270
2-Nitrophthalic hydrazide
HCID 1317308422-Amino-1,2,3,4-tetrahydrophthalazine-1,4-dione sodium salt dihydrate

Product 1

HCID 669903292-Amino-1,2,3,4-tetrahydro-1,4-phthalazinedione sodium salt

Reagents, catalysts & solvents 1

HCID 6336846Nickel aluminideCatalyst

Procedure

In the patent RU 2138264, there is described a method for obtaining compound III, that is 2-amino-1,2,3,4-tetrahydrophthalazine-1,4-dione sodium salt dihydrate and it includes transformation of 3-nitrophtalic acid anhydride by means of hydrazine hydrate into 2-nitrophthalic hydrazide which is transformed into 3-aminophthalohydrazide by means of hydrazine hydrate in alkaline medium at presence of nickel-aluminum alloy, thereafter there is performed molecular rearrangement to 2-aminophthalohydrazide by means of bromine under pressure. In the final stage there are mixed 2-amino-phthalohydrazide and NaOH solution at the temperature up to 85° C. thereafter the mixture is filtered and evaporated up to obtaining 2-amino-1,2,3,4-tetrahydro-1,4-phthalazinedione sodium salt dehydrate.

Workup

  1. filtrationthe mixture is filtered
  2. customevaporated up

Sources & evidence

ORD record
ord-403c782a2017465b8f1201570a76b30c
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08536171B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes