Hydrochloric Acid → HCID 15475386, compound

HRID 566880Notes

Reaction equation

HRID 566880 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH3:18])[C:13]=1[O:14][CH2:15][CH:16]=[CH2:17])[O:10][C:9](=[O:19])[CH:8]=[C:7]2[CH3:20])([O-])=O.[Sn](Cl)Cl.[Sn].Cl>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]2[C:11](=[C:12]([CH3:18])[C:13]=1[O:14][CH2:15][CH:16]=[CH2:17])[O:10][C:9](=[O:19])[CH:8]=[C:7]2[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 5352426Tin atomHCID 15475385HCID 15475385, compound

Product 1

HCID 15475386HCID 15475386, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Generally, the diazonium tetrafluoroborate intermediates are prepared by nitration of 7-hydroxycoumarin with nitric acid in sulfuric acid to give 6-nitro-4-8-dimethyl-7-hydroxycoumarin 1 (see Example 1 below) which is then o-allylated by treatment with allyl bromide and potassium carbonate in dimethylsulfoxide to produce 6-nitro-4,8-dimethyl-7-allyloxycoumarin 2 (see Example 2 below). The 6-nitro-4,8-dimethyl-7-allyloxycoumarin is then reduced by treatment with tin(II) chloride, tin, and concentrated hydrochloric acid in ethanol to give 6-amino-4,8-dimethyl-7-allyloxycoumarin 3 (see Example 3 below). Finally, 6-diazoniumtetrafluoroborate-4,8-dimethyl-7-allyloxycoumarin 4 is formed by treatment with sodium nitrite in tetrafluoroboric acid (see Example 4 below).

Sources & evidence

ORD record
ord-f4adc7151b4449f58005c1fccfbc2c03
Source dataset
uspto-grants-2001_01
Patent number
US06177424B1

Reaction notes

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