Ammonia → 3-Amino-5-methoxybenzamide

HRID 1515563Notes

Reaction equation

HRID 1515563 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].[CH3:12][O:13]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]([O:13][CH3:12])[CH:10]=1)[C:5]([NH2:7])=[O:6]

Participants

4

Reactant 3

HCID 222AmmoniaHCID 53002123-Methoxy-5-nitrobenzoic acidHCID 539884413-Amino-5-methylbenzamide

Product 1

HCID 594795273-Amino-5-methoxybenzamide

Procedure

Using a procedure analogous to that described for preparation of 89C, 93C was converted to an acid chloride, reacted with aqueous ammonia, and hydrogenated to give 93D. 1H NMR (400 MHz, CD3OD) δ ppm 3.76 (s, 3H) 6.45 (t, J=2.20 Hz, 1H) 6.71-6.74 (m, 1H) 6.77 (t, J=1.54 Hz, 1H); LC/MS 167 (M+H).

Sources & evidence

ORD record
ord-360195d0424a4fbca9f6be6c9c9e8758
Source dataset
uspto-grants-2012_07
Patent number
US08222453B2

Reaction notes

Loading…