Sodium Hydroxide → Urea

HRID 1168420Notes

Reaction equation

HRID 1168420 reaction equation
[C:1]([NH:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](Br)=[CH:7][C:6]=1[N+]([O-])=O)(=[O:3])C.[OH-].[Na+].BrC1C2C(=CC=CC=2)C(O)=C([N+:33]([O-])=O)C=1>>[NH2:33][C:1]([NH2:4])=[O:3].[N:4]1[C:5]2[C:14]3[C:9]([CH:8]=[CH:7][C:6]=2[O:3][CH:1]=1)=[CH:10][CH:11]=[CH:12][CH:13]=3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3484101-(acetylamino)-4-bromo-2-nitronaphtaleneHCID 115725344-bromo-2-nitronaphthalen-1-ol

Product 2

HCID 1176UreaHCID 3718558Naphth[1,2-d]oxazole

Procedure

When 1-(acetylamino)-4-bromo-2-nitronaphtalene was treated with aqueous sodium hydroxide as described above the product was 4-bromo-2-nitro-1-naphtol—i.e. substitution occurred instead of hydrolysis. Subsequent hydrogenation and treatment with urea yielded naphto[1,2-d]oxazoline in 44% overall yield.

Workup

  1. customsubstitution occurred instead of hydrolysis

Sources & evidence

ORD record
ord-273143351a584cd59646ea5989288403
Source dataset
uspto-grants-2003_09
Patent number
US06624186B2

Reaction notes

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