Formaldehyde → 4-Methyl-7-nitro-3,4-dihydro-2H-benzo[b][1,4]oxazine

HRID 990925Notes

Reaction equation

HRID 990925 reaction equation
[N+:1]([C:4]1[CH:13]=[CH:12][C:7]2[NH:8][CH2:9][CH2:10][O:11][C:6]=2[CH:5]=1)([O-:3])=[O:2].C=O.[BH3-][C:17]#N.[Na+]>>[CH3:17][N:8]1[C:7]2[CH:12]=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[O:11][CH2:10][CH2:9]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 184161517-Nitro-3,4-dihydro-2H-1,4-benzoxazine

Product 1

HCID 184161944-Methyl-7-nitro-3,4-dihydro-2H-benzo[b][1,4]oxazineYield 98%

Procedure

This compound was prepared by General Method 3 from 3,4-dihydro-7-nitro-2H-1,4-benzoxazine (1.15 g, 6.38 mmol), paraformaldehyde (1.92 g, 64.1 mmol) and NaBH3CN (1.95 g, 30.9 mmol) to afford 1.21 g (98%) of 3,4-dihydro-4-methyl-7-nitro-2H-1,4-benzoxazine, a yellow solid. Data for 3,4-dihydro-4-methyl-7-nitro-2H-1,4-benzoxazine: Rf 0.83 (11.5:1 CH2Cl2:MeOH); 1H NMR (400 MHz, CDCl3) δ 7.82 (dd, 1H, J=9.0, 2.6), 7.65 (d, 1H, J=3.4), 6.56 (d, 1H, J=8.9), 4.27 (t, 2H, J=4.6), 3.46 (t, 2H, J=4.5), 3.05 (s, 3H).

Sources & evidence

ORD record
ord-85f8ea09dbda42bba17e86b34fe3a840
Source dataset
uspto-grants-2002_10
Patent number
US06462038B1

Reaction notes

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