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Boric Acid → Benzo(g)pteridine-2,4(1H,3H)-dione, 7,8-dichloro-

HRID 126768
Notes
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Reaction equation

HRID 126768 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH2:9])=[C:4]([NH2:10])[CH:3]=1.O.[NH:12]1[C:20](=[O:21])[C:18](=O)[C:16](=O)[NH:15][C:13]1=[O:14].B(O)(O)O>C(O)(=O)C>[CH:3]1[C:2]([Cl:1])=[C:7]([Cl:8])[CH:6]=[C:5]2[N:9]=[C:16]3[NH:15][C:13](=[O:14])[NH:12][C:20](=[O:21])[C:18]3=[N:10][C:4]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7628Boric AcidHCID 167232,4,5,6(1H,3H)-Pyrimidinetetrone, monohydrateHCID 792974,5-Dichloro-1,2-phenylenediamine

Product 1

HCID 5487670Benzo(g)pteridine-2,4(1H,3H)-dione, 7,8-dichloro-Yield 99.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 10 g of 4,5-dichloro-o-phenylenediamine, 9 g of alloxan hydrate, 1.5 g of boric acid and 250 ml of glacial acetic acid was stirred overnight at room temperature to obtain a brown-black solution which was filtered. The yellow-buff crystalline solid was well washed with water to obtain 15.9 g of 7,8-dichloro-alloxazine melting at >370° C. A solution of 2 g of 7,8-dichloro-alloxazine in 10 ml of concentrated sulfuric acid was slowly heated to 240° C. and held there for 10 minutes. The mixture was cooled and poured onto ice and the mixture was made alkaline with sodium hydroxide addition. The mixture was extracted several times with ether to obtain 0.73 g of 2-amino-6,7-dichloro-quinoxaline as an orange crystalline solid melting at 220° C.

Workup

  1. customto obtain a brown-black solution which
  2. filtrationwas filtered
  3. washThe yellow-buff crystalline solid was well washed with water

Sources & evidence

ORD record
ord-fb47faf0040341b8bd2c4fd54bb0c4b5
Source dataset
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04254123

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes