3,4-Dihydro-2H-1-benzopyran-4-amine → 5-Fluoro-4-Chromanone

HRID 1363192Notes

Reaction equation

HRID 1363192 reaction equation
FC1C=CC=C2C=1[O:10]CCC2N.O1C2C(=CC=CC=2)C(N)CC1.FC1C=C2C(=CC=1)OCCC2N.ClC1C=C2C(=CC=1)OCCC2N.CC1C=C2C(=CC=1)OCCC2N.COC1C=C2C(=CC=1)OCCC2N.[F:73][C:74]1[CH:83]=[CH:82][CH:81]=[C:80]2[C:75]=1[CH:76](N)[CH2:77][CH2:78][O:79]2>>[F:73][C:74]1[CH:83]=[CH:82][CH:81]=[C:80]2[C:75]=1[C:76](=[O:10])[CH2:77][CH2:78][O:79]2

Participants

8

Reactant 7

HCID 49619573,4-Dihydro-2H-1-benzopyran-4-amineHCID 127921486-Methoxychroman-4-amineHCID 162444038-Fluorochroman-4-amineHCID 162444126-Chloro-chroman-4-ylamineHCID 162444136-fluoro-3,4-dihydro-2H-1-benzopyran-4-amineHCID 162444176-Methylchroman-4-amineHCID 597048985-Fluorochroman-4-amine

Product 1

HCID 454897955-Fluoro-4-Chromanone

Procedure

These amines were prepared via procedures described in Example 29 for the synthesis of 8-fluorochroman-4-amine. The corresponding chroman-4-ones were commercially available as advanced intermediates for the synthesis of chroman-4-amine, 6-fluorochroman-4-amine, 6-chlorochroman-4-amine, 6-methylchroman-4-amine, and 6-methoxychroman-4-amine. For the synthesis of 5-fluorochroman-4-amine, the intermediate 5-fluorochroman-4-one was obtained using procedures from GB 2355264, which also provided 7-fluorochroman-4-one. 7-Fluorochroman-4-one could be used in the synthesis of 7-fluorochroman-4-amine. Chroman-4-amine, 5-fluorochroman-4-amine, 6-fluorochroman-4-amine, 7-fluorochroman-4-amine, 5,8-difluorochroman-4-amine, and 6,8-difluorochroman-4-amine were resolved via the procedure described in Example 29 for the resolution of 8-fluorochroman-4-amine.

Sources & evidence

ORD record
ord-694aaad3b098485b86c23cf2a08cc62e
Source dataset
uspto-grants-2011_02
Patent number
US07884109B2

Reaction notes

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