5-Chloro-2-methylaniline → N-tert-butoxycarbonyl-5-chloro-2-methylaniline

HRID 1901780Notes

Reaction equation

HRID 1901780 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12](Cl)=[CH:11][C:10]=1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17]C1C=CC(C)=C(C=1)N.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([Cl:17])[CH:12]=[CH:11][C:10]=1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 72605-Chloro-2-methylanilineHCID 90495Di-tert-butyl dicarbonateHCID 14710386tert-Butyl (4-chloro-2-methylphenyl)carbamate

Product 1

HCID 4935530N-tert-butoxycarbonyl-5-chloro-2-methylanilineYield 77%

Procedure

N-tert-Butoxycarbonyl-4-chloro-2-methylaniline. By the procedure in Example 1, Part C, 28.3 g (0.2 mole) of 5-chloro-2-methylaniline was reacted with 48.1 g (0.22 mol) of di-tert-butyl dicarbonate to give 37.1 g (77% yield) of N-tert-butoxycarbonyl-5-chloro-2-methylaniline melting at 100°-102° C., after crystallizing from hexane.

Sources & evidence

ORD record
ord-14e555cbd48b4838a2711bdd127fa50e
Source dataset
uspto-grants-1996_11
Patent number
US05578634

Reaction notes

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