Ammonia → HCID 68968838, compound

HRID 1891569Notes

Reaction equation

HRID 1891569 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CO[C:9](=[O:20])[C:10]1[CH:15]=[CH:14][C:13](COC)=[N:12][C:11]=1[NH2:19].N.[O:22]1[CH2:26]CC[CH2:23]1>>[NH2:19][C:11]1[C:10]([CH2:9][OH:20])=[C:15]([CH2:23][O:22][CH3:26])[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 8028TetrahydrofuranHCID 21226445Aluminium lithium hydrideHCID 592553992-Amino-6-methoxymethyl-nicotinic acid methyl ester

Product 1

HCID 68968838HCID 68968838, compoundYield 100%

Procedure

To a mixture of lithium aluminum hydride (80%, 220 mg, 4.6 mmol) and tetrahydrofuran (5 mL) was added 2-amino-6-methoxymethyl-nicotinic acid methyl ester (300 mg, 1.5 mmol) described in Manufacturing Example 26-1-4 at 0° C., which was stirred for 20 minutes at the same temperature. An aqueous 28% ammonia solution was added dropwise to the reaction mixture at 0° C. The mixture was warmed to room temperature and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (260 mg, 100%).

Workup

  1. customdescribed in Manufacturing Example 26-1-4 at 0° C.
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-768cc8a0d3e5491ab436cbd72e2669b0
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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