Iodine → HCID 13321946, compound

HRID 1284893Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].S(=O)(=O)(O)O.[I:24](O)(=O)=O.II>C(O)(=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([I:24])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 90 °C

Procedure

2 g of 5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 3) in 20 ml of glacial acetic acid is combined with 0.5 ml of water, 0.12 ml of concentrated sulfuric acid, 336 mg of iodic acid, and 878 mg of iodine and agitated for 2.5 hours at 90° C. After concentrating the reaction mixture, the latter is combined with 50 ml of water, gently made alkaline with ammonia, and suctioned off, thus obtaining 2.81 g of 8-iodo-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 264°-266° C. under decomposition.

Workup

concentrationAfter concentrating the reaction mixture

Sources & evidence

ORD record: ord-ae45591ad4d24e028d5eb8ecb3528346
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04564610

Reaction notes

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