Hydroxyamine hydrochloride → tert-Butyl 2-Amino-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

HRID 1918908Notes

Reaction equation

HRID 1918908 reaction equation
C1(C(=[N:14][C:15]2[CH:24]=[CH:23][C:22]3[CH2:21][N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:18][C:17]=3[N:16]=2)C2C=CC=CC=2)C=CC=CC=1.NO.Cl>CO>[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][N:20]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:19][CH2:18][C:17]=2[N:16]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 58043757tert-Butyl 2-(Diphenylmethyleneamino)-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Product 1

HCID 58043778tert-Butyl 2-Amino-7,8-dihydro-1,6-naphthyridine-6(5H)-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 158a was added to a round-bottomed flask. MeOH (50 mL) and NH2OH HCl (1.76 g, 25.3 mmol) was added. The resulting mixture was stirred at RT for 5 hrs. The solvents were removed in vacuo and silica gel column (MeOH:DCM=10:90) gave 158b as dark oil, 851 mg (84%, 2 steps).

Workup

  1. customThe solvents were removed in vacuo and silica gel column (MeOH:DCM=10:90)

Sources & evidence

ORD record
ord-a58c1480639f4ce4b82b6516603f683b
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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