Ammonia → 3-Amino-5-fluorobenzamide

HRID 1515558Notes

Reaction equation

HRID 1515558 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9](C)[CH:10]=1)[C:5]([NH2:7])=[O:6].[F:12]C1C=C(C=C([N+]([O-])=O)C=1)C(O)=O.N>>[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:12])[CH:10]=1)[C:5]([NH2:7])=[O:6]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 27590473-Fluoro-5-nitrobenzoic acidHCID 539884413-Amino-5-methylbenzamide

Product 1

HCID 468353333-Amino-5-fluorobenzamide

Procedure

Using a procedure analogous to that described for preparation of 89C, 3-fluoro-5-nitrobenzoic acid was converted to an acid chloride, reacted with aqueous ammonia, and hydrogenated to give 91A. 1H NMR (400 MHz, CD3OD) δ ppm 6.55 (dt, J=10.99, 2.20 Hz, 1H) 6.79 (m, 1H) 6.95 (t, J=1.54 Hz, 1H); LC/MS 155 (M+H).

Sources & evidence

ORD record
ord-32a418406be54399ab9d44aa50ebdea5
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

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